Author(s): S.M. Ali, K. Ramesh and R.T. Borchardt
Title: Efficient enantioselective synthesis of carbocyclic nucleoside and prostaglandin synthons
Tetrahedron Lett. Vol. 31, No. 11, p. 1509-1512 (1990); ISSN: 0040-4039;

keywords: 4,5-Dihydroxycyclopent-2-en-1-on; 4,5-O-Cyclohexyliden-4,5-dihydroxycyclopent-2-enone; 4,5-Dihydroxy-2-cyclopentenone; 4,5-O-Isopropylidene-4,5-dihydroxycyclo-2-penten-1-one; 4,5-Dihydroxy-2-cyclopenten-1-one; 4,5-O-Isopropylidene-4,5-dihydroxycyclo-2-pentenone; D-Ribono-1,4-lacton; D-Lyxose; Glycolspaltung mit PCC; Pyridiniumchlorchromat
Abstract:
Simple and efficient enantioselective syntheses of two hydroxylated cyclopentenones, 2 and 10, which are useful intermediates for the synthesis of various carbocyclic nucleosides and prostaglandins, directly from readily available sugars are described.

Inventor(s): Akio Yasuno and Ryuji Tanaka
Title: D-Ribonolactone
(Tokyo Tanabe Seiyaku Co., Ltd.) US Pat. Appl. US 3,709,912, (09.01.1973); Patent Class.: C07d

keywords: Epimerisierung, D-ribonic acid, D-arabonic acid, D-Ribonolacton, iron D-ribonate, D-Ribono-1,4-lacton, D-Ribono-g-lacton
Anmeldung: 13.03.1969
korrespondierendes Patent: GB 1,266,786 vom 15.03.1969 (Klassifikation C07d).

Author(s): P. Smid, D. Noort, H.J.G. Broxterman, N.C.R. van Straten, G.A. van der Marel and J.H. van Boom
Title: Synthesis of L-glucose derivatives from D-glucose and L-arabinose
Recl. Trav. Chim. Pays-Bas Vol. 111, No. 12, p. 524-528 (1992); ISSN: 0165-0513 / 0034-186X;

keywords: Nef-reaction; D-glucurono-1,5-lactone; D-glucose; L-glucose; L-arabinose; 2,3,4,6-tetra-O-benzyl-L-glucopyranose; L-olivose; L-cladinose; 2,3,4,5,6-penta-O-benzyl-L-glucitol; penta-O-acetyl-L-glucopyranose; penta-O-acetyl-D-mannopyranose

Author(s): K.C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M.R.V. Finlay and Z. Yang
Title: Total Syntheses of Epothilones A and B via Macolactonization-based strategy
J. Am. Chem. Soc. Vol. 119, p. 7974-7991 (1997); ISSN: 0002-7863;

keywords: Oxidation von Alkoholen; Milde Oxidationsmethode; Schwefeltrioxid-Pyridin-Komplex; DMSO; Dimethylsulfoxid

Author(s): S.K. Johansen and I. Lundt
Title: Synthesis of Carbasugars from Aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes funktionalised at all five ring carbons
J. Chem. Soc., Perkin Trans. 1, p. 3615-3622 (1999); ISSN: 0300-922X;

keywords: radical cyclization forming carbasugars; 7,8-Dihydroxy-2-oxabicyco[3.3.0]octan-2-one
Abstract:
Starting from (1R,5R,8R)-8-acetoxy-2-oxabicyclo[3.3.0]oct-6-en-3-one (4) the syntheses of 5-deoxy-4a(R)-hydroxy-4a-carba-a-D-ribo-hexofuranose (17), 5-deoxy-4a(R)-hydroxy-4a-carba-a-D-lyxo-hexofuranose (21), 5-deoxy-4a(R)-hydroxy-4a-carba-a-D-xylo-hexofuranose (23) and 4a(R)-hydroxy-2-amino-2,5-dideoxy-4a(R)-hydroxy-4a-carba-a-D- arabino-hexofuranose (1) have been achieved. The methodology included OsO₄-catalysed dihydroxylation as well as regioselective epoxide opening followed by calcium borohydride reduction of the lactone moiety.

Inventor(s): S. Matsumoto and M. Miyazaki
Title: Process for preparing D-Ribose
(Tanabe Seiyaku Co., Ltd., Osaka, Japan) US Pat. Appl. US 3380901, (30.04.1968); Patent Class.: US-Cl.: 204-73; C07H3/02, C25B3/04

keywords: D-Ribose, elektrolytische Reduktion von D-Ribonolacton
Korrespondierende Patentschriften CH451900, GB1007642

Vergleiche Patent US 3312608 (US-Cl.: 204-73), 04.04.1967

Inventor(s): S. Sugasawa and S. Matsumoto
Title: Electrolytic process for preparing D-Ribose
(Tanabe Seiyaku Co., Ltd.) US Pat. Appl. US 3312608, (04.04.1967); Patent Class.: US-Cl.: 204-73; C08B37/00, C25B3/04

keywords: D-Ribose, elektrolytische Reduktion von D-Ribonolacton
Korrespondierende Patentschriften DE1205074, FR1381987, GB993451

Vergleiche Patent US 3380901 (US-Cl. 204-73), 30.04.1968

Author(s): D. Liu and C.A. Caperelli
Title: A new synthesis of D-Ribonolactone from D-Ribose by Pyridinium chlorochromate Oxidation
Synthesis, p. 933-934 (1991); ISSN: 0039-7881;

keywords: Oxidation mit PCC; Pyridiniumchlorochromat; D-Ribonolacton; D-Ribono-g-lacton; 2,3-O-Cyclohexylidene-D-ribonolactone; 2,3-O-Cyclohexyliden-D-ribono-g-lacton; 2,3-O-Cyclohexyliden-L-erythruronosäure; 2,3-O-Cyclohexyliden-L-erythruronolacton; Periodatspaltung; PDC-Oxidation; 2,3-O-Cyclohexylidene-D-ribose; 2,3-O-Cyclohexyliden-D-ribofuranose; Glycolsplatung mit PCC
Abstract:
2,3-O-Cyclohexylidene-D-ribonolactone is prepared directly from 2,3-O-cyclohexylidene-D-ribose by pyridinium chlorochromate (PCC) oxidation in 55-60 % yield.

Author(s): C.L. Marien, E.L. Esmans, F. Lemière and R.A. Dommisse
Title: Reinvestigation of the Synthesis of (2R,3R)-2,3-O-Cyclohexylidenedioxy-4-cyclopentenone as possible building blocks for the synthesis of carbocyclic nuclosides
Synth. Commun. Vol. 27, No. 2, p. 205-224 (1997); ISSN: 0039-7911;

keywords: cis-4,5-Dihydroxy-2-cyclopenten-1-on; 4,5-O-Cyclohexyliden-4,5-dihydroxy-2-cyclopenten-1-on; D-Ribonolacton; D-Ribono-g-lacton; 2,3-O-Cyclohexylidene-D-ribonolactone; 2,3-O-Cyclohexyliden-D-ribono-g-lacton; 2,3-O-Cyclohexyliden-L-erythruronosäure; 2,3-O-Cyclohexyliden-L-erythruronolacton; Periodatspaltung; 4,5-O-Cyclohexylidendioxy-2-cyclopenten-1-on; 2,3-O-Cyclohexylidendioxy-4-cyclopenten-1-on

Author(s): J.Y. Kim, J.E. Nam Shin and K.H. Chun
Title: An efficient synthesis of 4-O-tert.-Butyldimethylsilyl-2,3-O-isopropylidene-L-threose and erythrose: useful chiral building blocks in synthesis
Bull. Korean Chem. Soc. Vol. 17, No. 5, p. 478-480 (1996); ISSN: 0253-2964;

keywords: 4-O-tert.-Butyldimethylsilyl-2,3-O-isopropyliden-L-threose; 4-O-tert.-Butyldimethylsilyl-2,3-O-isopropyliden-L-erythrose

Author(s): J.G. Buchanan, A.R. Edgar, M.J. Power and P.D. Theaker
Title: Synthesis of D-ribofuranosyl derivatives of dimethyl maleate and of ethyl acetate as C-nucleoside precursors
Carbohydr. Res. Vol. 38, p. C22-C24 (1974); ISSN: 0008-6215;

keywords: 2,3,5-Tri-O-benzyl-D-ribofuranose; D-Ribose

Author(s): M.S. Wolfe and R.T. Borchardt
Title: S-Adenosyl-L-homocysteine hydrolase as a target for antiviral chemotherapy
J. Med. Chem. Vol. 34, No. 5, p. 1521-1530 (1991); ISSN: 0022-2623;

keywords: Carbanucleoside; Aristeromycin; Neplanomycin A

Author(s): H. Akimoto, H. Nomura, M. Yoshida, N. Shindo-Okada, A. Hoshi and S. Nishimura
Title: Queuine analogues. Their synthesis and Inhibition of growth of mouse L5178Y cells in vitro
J. Med. Chem. Vol. 29, p. 1749-1753 (1986); ISSN: 0022-2623;

keywords: Carbanucleoside; 4,5-Dihydroxycyclpent-1-en-3-yl-

Author(s): S.A. Miller and A.R. Chamberlin
Title: Enantiomerically pure polyhydroxylated Acyliminium ions. Syntheses of Glycosidase inhibitors (-)-Swainsonine and (+)-Castanospermine
J. Am. Chem. Soc. Vol. 112, p. 8100-8112 (1990); ISSN: 0002-7863;

keywords: 2,3-O-Cyclohexyliden-D-Ribono-1,4-lacton; 2,3-O-Cyclohexylidene-D-Ribono-1,4-lactone; 2,3-O-Cyclohexyliden-D-Ribono-g-lacton; 2,3-O-Cyclohexyliden-D-lyxose

Author(s): A.-M. Sepulchre, A. Gateau and S.D. Géro
Title: Synthèse du 5-Azido-1,4-di-O-benzyl-5-désoxy-2-O-p-tolylsulfonyl-D-ribitol et du 2-Azido-2-désoxy-3,4-O-isopropylidène-1-O-(tétrahydropyran-2-yl)-5-O-p-tolylsulfonyl-L-arabinitol à partir de la D-Ribono-1,4-lactone
Carbohydr. Res. Vol. 24, p. 311-318 (1972); ISSN: 0008-6215;

keywords: 2,3-O-Cyclohexyliden-D-Ribono-1,4-lacton; 2,3-O-Cyclohexylidene-D-Ribono-1,4-lactone; 2,3-O-Cyclohexyliden-D-Ribono-g-lacton; 3,4-O-Cyclohexyliden-D-Ribono-1,5-lacton; 3,4-O-Cyclohexylidene-D-Ribono-1,5-lactone; 3,4-O-Cyclohexyliden-D-Ribono-d-lacton

Author(s): S. Jacobsen and C. Pedersen
Title: Dioxolanylium ions derived from Carbohydrates. I. Reactions with water and with bromide ions
Acta Chem. Scand. B Vol. 28B, p. 866-872 (1974); ISSN: 0302-4369;

keywords: methyl 3,4-O-benzylidene-b-D-arabinopyranoside; methyl 2,3-O-benzylidene-a-D-arabinopyranoside; 2,3-O-benzylidene-b-D-ribopyranoside

Author(s): M.C.B.V. de Souza, M.N. da Silva and V.F. Ferreira
Title: A two-step preparation of a new C4 chiral building block derivative of D-Erythronic acid
Synlett, No. 20, p. 1339-1340 (1998); ISSN: 0936-5214;

keywords: D-Erythronsäure; D-Erythronsäure-1,4-lacton; D-Erythronsäure-g-lacton; 1,2; 3,4-Di-O-Isopropyliden-D-erythronsäure; 2,3; 5,6-Di-O-isopropyliden-D-Gluconsäuremethylester; 3,4; 5,6-Di-O-isopropyliden-D-Gluconsäuremethylester

Author(s): A. Gypser, M. Flasche and H.D. Scharf
Title: D-Eythronolactone and 2,3-O-Isopropylidene-L-erythrose as C4 building units: an efficient synthesis of both enantiomers of endo-Brevicomin and its 7-vinyl analogues
Liebigs Ann. Chem., p. 775-780 (1994); ISSN: 0170-2041;

keywords: 2,3-O-Isopropyliden-L-erythrose; Methylen-Wittig; D-Erythronolacton; D-Erythrono-1,4-lacton; D-Erythronsäurelacton

Author(s): A. Gypser, M. Petereck and H.D. Scharf
Title: D-Eythronolactone as a C4 building unit. Part 2. A short and efficient synthesis of both enantiomers of epi-muricatacin, a diastereoisomer of native acetogenin from Annona muricata
J. Chem. Soc., Perkin Trans. 1, p. 1013-1016 (1997); ISSN: 0300-922X;

keywords: 2,3-O-Isopropyliden-D-erythrose; Ketalisierung/Acetalisierung von Erythronolacton; 2,3-O-Isopropyliden-D-erythronolacton; 2,3-O-Isopropyliden-D-erythronsäuremethylester; D-Erythronolacton; D-Erythrono-1,4-lacton; D-Erythronsäurelacton; Methylen-Wittig

Author(s): N. Cohen, B.L. Banner, R.J. Lopresti, F. Wong, M. Rosenberger, Y.-Y. Lui, E. Thom and A.A. Liebman
Title: Enantiospecific syntheses of leukotrienes C4, D4, and E4 and [14,15-3H2]Leukotriene E4 dimethyl ester
J. Am. Chem. Soc. Vol. 105, p. 3661-3672 (1983); ISSN: 0002-7863;

keywords: L-Ascorbinsäure; Vitamin C; 2,3-O-Isopropyliden-D-erythrose; Ketalisierung/Acetalisierung von Erythronolacton; 2,3-O-Isopropyliden-D-erythronolacton; D-Erythronolacton; D-Erythrono-1,4-lacton; D-Erythronsäurelacton; DIBAH-Reduktion von Erythronolacton

Author(s): H.J. Bestmann and L. Bauriegel
Title: Chirale Erythrose- and 2-Desoxyribose-Synthesebausteine der D- and L-Reihe aus Mesoweinsäure
Tetrahedron Lett. Vol. 36, No. 6, p. 853-856 (1995); ISSN: 0040-4039;

keywords: meso-Weinsäure; tartratic acid; Acetalisierung/Ketalisierung mit Acetaldehyd-dimethylacetal; 2,3-O-Methylethyliden-D-erythrose; Erythruronolacton

Author(s): H. Sano and S. Sugai
Title: Synthesis of an optically active carbocyclic derivative of (+)-Hydantocidin
Tetrahedron: Asymmetry Vol. 6, No. 5, p. 1143-1150 (1995); ISSN: 0957-4166;

keywords: D-Gulonsäure-1,4-lacton; D-Gulonsäure-g-lacton; 2,3; 5,6-Di-O-Isopropyliden-D-Gulono-1,4-lacton; 2,3-O-Isopropyliden-D-Gulono-1,4-lacton; Natriumperiodatspaltung; 2,3-O-Isopropyliden-L-Erythruronolacton; 2,3-O-Isopropyliden-L-Erythruronolacton-methylglycosid; 2,3-O-Isopropyliden-L-Erythruronoisopropylglycosid; Fujimoto-Belleau-Reaktion; Carbocyclische Nucleoside; 4,5-O-Isopropyliden-4,5-dihydroxy-2-cyclopenten-1-on; 4,5-O-Isopropyliden-4,5-dihydroxy-1-cyclopenten-3-on; cis-4,5-Dihydroxy-2-cyclopenten-1-on; cis-4,5-Dihydroxycyclopent-2-en-1-on; 4,5-Dihydroxy-2-cyclopentenone; 4,5-O-Cyclohexylidene-4,5-dihydroxycyclo-2-penten-1-one; 4,5-Dihydroxy-2-cyclopenten-1-one; 4,5-O-Isoproylidene-4,5-dihydroxycyclo-2-pentenone; 2,3-O-Isopropylidenedioxy-4-cyclopenten-1-on; 2,3-O-Isopropylidene-2,3-dihydroxy-4-cyclopenten-1-on; 2,3-O-Isopropylidene-2,3-dihydroxy-4-cyclopenten-1-on; 4,5-O-Isopropylidenedioxy-2-cyclopenten-1-on; D-Gulonolacton; D-Gulono-1,4-lacton; D-Gulono-g-lacton

Author(s): C.L. Leese and H.N. Rydon
Title: Polyazanaphthalenes. Part I. Some derivatives of 1:4:5-Triazanaphthalenes and Quinoxaline
J. Chem. Soc., p. 303-308 (1955); ISSN: 0368-1769 / 0300-9246;

keywords: 2-quinoxalinaldehyde; 2-quinoxalincarbaldehyde; 2-Formylquinoxaline; 2-(d-arabino-tetraoxybutyl)-quinoxaline; sodium periodate; periodate cleavage; glycol cleavage; condensation of 2,3-diaminopyridine with 1,3-dichloracetone; reaction of o-phenylendiamine with sugars

Author(s): G. Stork and S. Raucher
Title: Chiral synthesis of prostaglandins from Carbohydrates. Synthesis of (+)-15-(S)-Prostaglandin A2
J. Am. Chem. Soc. Vol. 98, p. 1583-1584 (1976); ISSN: 0002-7863;

keywords: 2,3-O-Isopropyliden-L-erythrose; Vinyl-Gringnard-Addition an 2,3-O-Isopropyliden-L-erythrose; Claisen-Umlagerung; [3.3]-sigmatrophe Umlagerung; Kohlensäureester als Schutzgruppe

Author(s): B.R. Baker and K. Hewson
Title: Synthesis of potential anticancer agents. VIII. Nucleosides derived from L-Rhamnofuranose
J. Org. Chem. Vol. 22, p. 966-971 (1957); ISSN: 0022-3263;

keywords: 2,3-O-Isopropyliden-L-erythrose; 2,3-O-Isopropyliden-L-rhamnofuranose; 5-O-Benzoyl-L-rhamnofuranose

Author(s): J.N. Baxter and A.S. Perlin
Title: 2,3-O-Isopropylidene-L-erythrotetruronic acid and -L-erythrose, and the methyl D-erythro- and D-threo-tetrofuranoside
Can. J. Chem. Vol. 38, p. 2217-2225 (1960); ISSN: 0008-4042;

keywords: 2,3-O-isopropylidene-L-erythruronic acid; 2,3-O-isopropyliden-L-erythruronolactone; 2,3-O-isopropyliden-L-erythrose; 2,3-O-isopropyliden-L-rhamnofuranose; periodate cleavage; glycol cleavage with sodium meta-periodate; 3,4-O-isopropylidene-D-arabinose; D-erythrose; L-erythrose; D-erythrurono-1,4-lactone; D-erythrurono-g-lactone; 2,3-O-isopropyliden-L-rhamnitol; methyl a-D-erythrotetrofuranoside; methyl a-D-erythrotetrofuranoside-2,3-O-carbonate

Author(s): A.R. Chamberlin and J.Y.L. Chung
Title: Enantioselective synthesis of seven pyrrolizidine diols from a single precursor
J. Org. Chem. Vol. 50, p. 4425-4431 (1985); ISSN: 0022-3263;

keywords: 2,3-O-Cyclohexyliden-L-erythruronsäure; 2,3-O-Cyclohexyliden-L-erythruronolacton; 2,3-O-Cyclohexyliden-L-erythrose; L-Erythrurono-1,4-lacton; L-Erythrurono-g-lacton; Methyl 2,3-O-Cyclohexyliden-a-D-Erythruronofuranosid; 2,3-O-Cyclohexyliden-a-D-Erythrotetrofuranosidmethylglycosid

Author(s): V. Jäger and B. Häfele
Title: Synthese aller optisch aktiver Olefin-Bausteine aus D-Ribonolacton: Isopropyliden-Derivate von D-erythro-pentendi- and -triolen (cis-4-substituierte 5-Vinyldioxolane)
Synthesis, p. 801-806 (1987); ISSN: 0039-7881;

keywords: 2,3-O-Isopropyliden-D-ribono-1,4-lacton; Silylester als Schutzgruppe; Methylen-Wittig an 2,3-O-Isopropyliden-D-erythrose; 2,3-O-Isopropyliden-L-erythruronolacton; 2,3-O-Isopropyliden-L-erythruronsäuremethylester
vergleiche Häfele, B.; Schröter, D.; Jäger, V.: Angew. Chem. 98, 1986, 89-90.

Author(s): K. Narkunan and M. Nagarajan
Title: Preparation of sugar-derived b-Keto phosphonates and their use in the synthesis of higher sugars
J. Org. Chem. Vol. 59, p. 6386-6390 (1994); ISSN: 0022-3263;

keywords: b-Ketophosphonate aus Estern durch nucleophile Substitution mit Lithiummethyldimethylphosphonat; Methylphosphonsäuredimethylester; 2,3; 4,5-Di-O-Isopropyliden-D-arabinonsäuremethylester

Author(s): P. Griess and G. Harrow
Title: Über die Einwirkung aromatischer Diamine auf Zuckerarten
Ber. Dtsch. Chem. Ges. Vol. 20, p. 2205-2213 (1887); ISSN: 0365-9496;

keywords: 2-(d-arabino-tetraoxybutyl)-quinoxaline; 2-(d-arabino-tetrahydroxybutyl)-quinoxaline; reaction of o-phenylendiamine with sugars

Author(s): N. Cohen, B.L. Banner, A.J. Laurenzano and L. Carozza
Title: 2,3-O-Isopropylidene-D-Erythronolactone
Org. Synth. Coll. Vol. Vol. 63, p. 127-135 (1985);

keywords: L-Ascorbinsäure; Vitamin C; Ketalisierung/Acetalisierung von Erythronolacton; 2,3-O-Isopropyliden-D-erythronolacton; D-Erythronolacton; D-Erythrono-1,4-lacton; D-Erythronsäurelacton
CAS-No. von 2,3-O-Isopropyliden-D-Erythronolacton [25581-41-3]

Author(s): B. Häfele, D. Schröter and V. Jäger
Title: Synthese von erythro-D- and -L-4-Pententriolen; selektive Epoxyallylalkohol-Hydrolyse unter Retention oder zweifacher Inversion (Enantiomerisierung)
Angew. Chem. Vol. 98, No. 1, p. 89-90 (1986); ISSN: 0044-8249;

keywords: D-Ribono-1,4-lacton; D-Ribono-g-lacton; 2,3-O-Isopropyliden-D-ribono-1,4-lacton; erythro-2,3-Dihydroxy-4-pentencarbonsäure; 1,2,3-Trihydroxy-4-buten; 1,4-Pentadien-3-ol; Divinylcarbinol; Sharpless-Epoxidierung; Methylen-Wittig an 2,3-O-Isopropyliden-D-Erythruronolacton
vergleiche Jäger, V.; Häfele, B.: Synthesis 1987, 801-806.

Author(s): R. Lohmar and K.P. Link
Title: Note on the reaction of d-Glucosamine with o-Phenylenediamine
J. Biol. Chem. Vol. 150, p. 351-352 (1943); ISSN: 0021-9258;

keywords: 2-Quinoxalinaldehyde; 2-Quinoxalincarbaldehyde; 2-(d-arabino-tetraoxybutyl)-quinoxaline; periodate cleavage; glycol cleavage; 2-Formylquinoxaline

Author(s): H. Ohrui, M. Konno and H. Meguro
Title: Synthesis of (4S,5S)-4,5-Dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one from D-Ribose
Agric. Biol. Chem. Vol. 51, No. 2, p. 625-626 (1987);

keywords: Neplanocin A; Pentenomycin; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopenten-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopenten-1-on; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopenten-1-on; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopenten-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropylidencyclopent-2-en-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropylidencyclopent-4-en-1-on; (2S,3S)-2,3-Isopropylidendioxycyclopent-4-en-1-on; (4S,5S)-4,5-Isopropylidendioxycyclopent-2-en-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopentenon; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopentenon; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopentenon; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopentenon

Author(s): T. Hudlicky, M.G. Natchus and T.C. Nugent
Title: Improved practical synthesis of a prostaglandin and carbocyclic nucleoside synthon
Synth. Commun. Vol. 22, No. 1, p. 151-157 (1992); ISSN: 0039-7911;

keywords: Neplanocin A; Pentenomycin; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopenten-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopenten-1-on; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopenten-1-on; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopenten-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropylidencyclopent-2-en-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropylidencyclopent-4-en-1-on; (2S,3S)-2,3-Isopropylidendioxycyclopent-4-en-1-on; (4S,5S)-4,5-Isopropylidendioxycyclopent-2-en-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopentenon; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopentenon; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopentenon; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopentenon; Erythruronolacton; Erythruronsäure-1,4-lacton; Erythruronolactonacetal; Erythruronsäure-1,4-lacton; Acetalisierung /Ketalsierung von Erythrurono-g-lacton

Author(s): M. Godskesen, I. Lundt and I. Søtofte
Title: Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols
Tetrahedron: Asymmetry Vol. 11, No. 2, p. 567-579 (2000); ISSN: 0957-4166;

keywords: D-Lyxonsäure-g-lacton; 2,3-O-Isopropyliden-D-Lyxonsäure-1,4-lacton; D-Lyxonsäure-Kaliumsalz; D-Lyxonsäuremethylester; Methyl-D-Lyxonat; 2,3; 4,5-O-Diisopropyliden-D-Lyxonsäuremethylester; kinetisch gesteuerte, selektive Abspaltung einer terminalen Isopropyliden-Schutzgruppe; 5-Amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-ribono-1,5-lactam; 5-Amino-5-deoxy-2,3-O-isopropylidene-4-O-p-toluenesulfonyl-D-ribono-1,5-lactam; 5-Amino-5-deoxy-2,3-O-isopropylidene-4-O-trifluoromethanesulfonyl-D-ribono-1,5-lactam; 4-Amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxono-1,4-lactam; 6-Amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo-hexitol, ditosylate; 5-Amino-4-azido-4,5-dideoxy-2,3-O-isopropylidene-L-lyxono-1,5-lactam; 4-Amino-1,4,5-trideoxy-1,5-imino-L-lyxitol, ditosylate; 2,3-O-Isopropylidene-D-lyxono-1,4-lactone; 2,3-O-Isopropylidene-5-O-methanesulfonyl-D-lyxono-1,4-lactone; 5-Amino-5-deoxy-2,3-O-isopropylidene-D-lyxono-1,5-lactam; 5-Amino-5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-lyxono-1,5-lactam; 4-Amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-ribono-1,4-lactam; 6-Amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol, ditosylate; N-Ethyl-5-amino-5-deoxy-2,3-O-isopropylidene-D-ribono-1,5-lactam; N-Ethyl-5-amino-5-deoxy-2,3-O-isopropylidene-4-O-trifluoromethanesulfonyl-D-ribono-1,5-lactam; Treatment of N-ethyl-5-amino-5-deoxy-2,3-O-isopropylidene-4-O-trifluoromethanesulfonyl-D-ribono-1,5-lactam 19 with tetrabutylammonium cyanide
Abstract:
Reaction of 4-O-sulfonylated 2,3-O-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-O-isopropylidene-L-lyxo- or -L-ribo-1,4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyano-lactams with LiAlH₄ gave 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-lyxo- or -L-ribo-hexitol, respectively. The 6-amino-1,4,5,6-tetradeoxy-1,4-imino-L-ribo-hexitol was found to be a moderate inhibitor of a-L-fucosidase with a K_i of 110 mM.

Author(s): P.A. Zunszain and O. Varela
Title: Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
Tetrahedron: Asymmetry Vol. 11, No. 3, p. 765-771 (2000); ISSN: 0957-4166;

keywords: 5-O-tert-Butyldiphenylsilyl-4-thio-L-lyxono-1,4-lactone; 2,3-Di-O-benzoyl-5-O-tert-butyldiphenylsilyl-4-thio-L-lyxono-1,4-lactone; (4R)-4-(tert-Butyldiphenylsilyloxymethyl)-4-thiobutyro-1,4-lactone ((5R)-dihydro-5-(tert-butyldiphenylsilyloxymethyl)-2(3H)-thiophenone); (4S)-(+)-4-Hydroxymethyl-1,4-butyrolactone; ((5S)-dihydro-5-(hydroxymethyl)-2-(3H)-furanone); (4S)-(+)-4-(p-Tolylsulfonyloxymethyl)-1,4-butyrolactone ((5S)-(+)-dihydro-5-(p-tolylsulfonyloxymethyl)-2(3H)-furanone); Methyl (4S)-4,5-epoxipentanoate; Methyl (4R)-4,5-epithiopentanoate; (4R)-Acetoxymethyl-4-thiobutyro-1,4-lactone ((5R)-dihydro-5-(acetoxymethyl)-2(3H)-thiophenone); (4R)-Hydroxymethyl-4-thiobutyro-1,4-lactone ((5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone) and its tert-butyldiphenylsilyloxy derivative
Abstract: Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI₂-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8).

Author(s): M.J. Comin and J.B. Rodriguez
Title: First Synthesis of (-)-Neplanocin C
Tetrahedron Vol. 56, No. 27, p. 4639-4649 (2000); ISSN: 0040-4020;


Abstract:
(-)-Neplanocin C (4), a minor component of the neplanocin family of antibiotics and a lead drug for the design of several conformationally constrained nucleosides analogues, was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in twelve steps. The proton NMR spectrum of 4 was in agreement with the corresponding natural product. Calculated coupling constants obtained from ab initio molecular modeling studies and from previously published X-ray structure of neplanocin C also corresponded to the spectroscopic data.

Author(s): J.B. Rodriguez
Title: Chiral 1,4-Dicarbonyl-2,3-O-Isopropylidene Derivatives. Rapid Racemization on Standing
Tetrahedron Vol. 55, No. 8, p. 2157-2170 (1999); ISSN: 0040-4020;


Abstract:
1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported. 1-Deoxy-3,4-O-isopropylidene-6-O-trityl--erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)--erythro-hexo-2,5-diulose were synthesized from -ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing.

Author(s): V. Popsavin, S. Grabez, B. Stojanovic, M. Popsavin, V. Pejanovic and D. Miljkovic
Title: Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride
Carbohydr. Res. Vol. 321, No. 1-2, p. 110-115 (1999); ISSN: 0008-6215;

keywords: 3,5-Di-O-benzyl-1,2-O-cyclohexylidene-a-D-xylofuranose; 3,5-Di-O-benzyl-D-xylofuranose; 3,5-Di-O-benzyl-2-O-methanesulfonyl-D-xylofuranose; Methyl 3,5-di-O-benzyl-a-D-lyxofuranoside; Methyl a-D-lyxofuranoside; Methyl a-D-lyxopyranoside; Benzyl 3,5-di-O-benzyl-a- and b-D-lyxofuranoside; 3,5-Di-O-benzyl-D-lyxofuranose; D-Lyxose
Abstract:
Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene-a-D-xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected -lyxofuranosides. These compounds were finally converted to methyl a-D-lyxopyranoside or to D-lyxose.

Author(s): Z. Ahmed, H. Sasahara, S.H Bhuiyan, T. Saiki, T. Shimonishi, G. Takada and K. Izumori
Title: Production of D-lyxose from D-glucose by microbial and enzymatic reactions
J. Biosci. Bioengineering Vol. 88, No. 6, p. 676-678 (1999); ISSN: 1389-1723;

keywords: Glucose; Isomerization; Enzymes; Bacteria; Fungi; Separation; Column chromatography; Biodegradation; Crystallization; High performance liquid chromatography; Nuclear magnetic resonance spectroscopy; Infrared spectroscopy; Optical rotation; Arabitol; Lyxose; Ribose isomerase; Glucose; Isomerization; Enzymes; Bacteria; Fungi; Separation; Column chromatography; Biodegradation; Crystallization; High performance liquid chromatography; Nuclear magnetic resonance spectroscopy; Infrared spectroscopy; Optical rotation; Arabitol; Lyxose; Ribose isomerase
Abstract:
D-Arabitol was first prepared from D-glucose using Candida famata R28. The reaction gave 5.0% D-arabitol from 10.0% D-glucose. D-Arabitol was then almost completely converted to D-xylulose using Acetobacter aceti IFO 3281. Finally, D-lyxose was prepared from D-xylulose enzymatically using L-ribose isomerase from toluene-treated cells of Acinetobacter sp. strain DL-28. The isomerization reaction progressed steadily and the concentration of D-xylulose increased from 1.0 to 10.0%. About 70% of D-xylulose was converted to D-lyxose in all cases. Separation of residual D-xylulose from the reaction mixture is very difficult to achieve by column chromatography, but D-xylulose could be selectively degraded easily using Saccharomyces cerevisiae IFO 0841. The product was crystallized and was confirmed to be D-lyxose by HPLC, 13C-NMR spectra, IR spectra analysis, and optical rotation measurement.

Author(s): S.H Bhuiyan, Z. Ahmed, M. Utamura and K. Izumori
Title: New method for the production of L-lyxose from ribitol using microbial and enzymatic reactions
J. Ferment. Bioengineering Vol. 86, No. 5, p. 513-516 (1998); ISSN: 0922-338X;

keywords: Sugars; Oxidation; Escherichia coli; Bioconversion; Enzyme immobilization; Substrates; Biodegradation; Purification; High performance liquid chromatography; Infrared spectroscopy; Nuclear magnetic resonance spectroscopy; Optical rotation; Crystallization; Ribitol; Rhamnose isomerase; Tagatose; Epimerase; Lyxose; Ribulose
Abstract:
L-Lyxose was prepared from ribitol by a new method comprising a potent microbial oxidation reaction to convert ribitol to L-ribulose, epimerization of the L-ribulose to L-xylulose, and isomerization of the L-xylulose to produce L-lyxose. The complete transformation of ribitol to L-ribulose was achieved using washed cells of Acetobacter aceti IFO 3281 at high substrate concentrations ranging from 5-20%. The L-ribulose produced was then used as the substrate for the production of r-lyxose using immobilized L-rhamnose isomerase (L-RI) of Pseudomonas sp. strain LL172 and immobilized n-tagatose 3-epimerase (D-TE) of recombinant Escherichia coli JM 105. At equilibrium, the yield of L-lyxose from L-ribulose was determined to be about 60%, and the product could be isolated easily from the reaction mixture after degradation of ketoses using Pseudomonas sp. 172a. Following various product purification steps, about 5.0 g L-Lyxose crystals were recovered from 10.0 g ribitol in a flask reaction. The crystallized product was finally identified by HPLC, IR spectrum, NMR, and optical rotation measurements.

Author(s): K.N. Drew, J. Zajicek, G. Bondo, B. Bose and A.S. Serianni
Title: ¹³C-labeled aldopentoses: detection and quantitation of cyclic and acyclic forms by heteronuclear 1D and 2D NMR spectroscopy
Carbohydr. Res. Vol. 307, No. 3-4, p. 199-209 (1998); ISSN: 0008-6215;


Abstract:
¹H-Decoupled ¹³C NMR spectra (150 MHz) of the simple aldopentoses (M solutions in D₂O, 28 °C) selectively labeled with ¹³C at C-1 (D-(1-¹³C)arabinose 1, D-(1-¹³C)lyxose 2, D-(1-¹³C)ribose 3, D-(1-¹³C)xylose 4) contain six enriched C-1 signals that were attributed to four cyclic (a- and b-furanoses and pyranoses) and two acyclic (aldehyde, hydrate) forms. Spectral data were collected and processed in a fashion to permit accurate quantitation of the cyclic and acyclic forms. Percentages of forms varied with pentose structure: a-furanose (0.8-7.4 %), b-furanose (0.6-13.2 %), a-pyranose (20.2-70.8 %), b-pyranose (26.9-62.0 %), hydrate (0.063-0.095 %), aldehyde (0.009-0.042 %). Aldehyde was least abundant in solutions of D-xylose and most abundant in solutions of D-ribose, and the hydrate/aldehyde ratio was higher for D-arabinose, D-lyxose, and D-xylose (6.3-7.8) than for D-ribose (2.1). Heteronuclear 2D HMQC-TOCSY and HCCH-TOCSY spectra were also obtained on several selectively and uniformly ¹³C-labeled model saccharides, respectively, to evaluate the advantages and limitations of these isotope-aided methods to detect ¹H signals of specific forms in solution. These methodologies can be extended to studies of suitably ¹³C-labeled oligosaccharides and oligonucleotides.

Author(s): G. Hodosi and P. Ková
Title: Manipulation of free carbohydrates via stannylene acetals. Preparation of b-per-O-acyl derivatives of D-mannose, D-rhamnose, 6-O-trityl-D-talose, and D-lyxose
Carbohydr. Res. Vol. 303, No. 2, p. 239-243 (1997); ISSN: 0008-6215;

keywords: Stannylene complexes; 1,2-O-cis-stannylene acetals; D-mannose; D-rhamnose; D-talose; D-lyxose
Abstract:
A simple and high-yielding method for the preparation of 1-O--acyl derivatives of carbohydrates with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2-O-cis stannylene acetals, when treated with dibutyltin oxide. These acetals can be acylated with retention of configuration at the anomeric position.

Author(s): L. Dubois and R.H. Dodd
Title: Stereocontrolled synthesis of aziridine-2-lactones from D-ribose and D-lyxose
Tetrahedron Vol. 49, No. 4, p. 901-910 (1993); ISSN: 0040-4020;


Abstract:
The synthesis of (1S,4S,5R)-N-acetyl-4-methoxymethyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 15a, an optically pure, cyclic analogue of aziridine-2-carboxylates, is described starting from D-ribose. Key steps include triphenylphosphine-promoted conversion of a 3-azido-2-tosyl-D-xylofuranoside (10a) to its corresponding 2,3-aziridine 12a, selective cleavage of a 1-O-t-butyldimethylsilyl blocking group followed by TPAP oxidation of the anomeric hemiacetal group to the lactone 15a. The procedure is directly applicable to D-lyxose to give the enantiomerically pure (1R,4S,5S) isomer of 15a, 15b.

Author(s): B. Lacourt-Gadras, M. Grignon-Dubois and B. Rezzonico
Title: Nouvelle voie d'accès au D-ribose et au D-lyxose
Carbohydr. Res. Vol. 235, p. 281-288 (1992); ISSN: 0008-6215;

Author(s): J. Wu and A.S. Serianni
Title: D-Penturonic acids: solution studies of stable-isotopically enriched compounds by ¹H- and ¹³C-n.m.r. spectroscopy
Carbohydr. Res. Vol. 210, p. 51-70 (1991); ISSN: 0008-6215;


Abstract:
Methyl -pentofuranosides were prepared by Fischer glycosidation of the aldopentoses D-arabinose, D-lyxose, D-ribose, D-xylose, and 2-deoxy-D-erythro-pentose, and oxidized with O₂ over a platinum oxide catalyst to give the corresponding methyl -pentofuranosiduronic acids. After purification by anion-exchange chromatography, these glycosides were hydrolyzed to give the corresponding D-penturonic acids [D-arabinuronic acid (1), D-lyxuronic acid (2), D-riburonic acid (3), D-xyluronic acid (4), and 2-deoxy-D-erythro-penturonic acid (5)] in 80 % yield based on the starting pentofuranoside. 1-¹³C-Substituted D-aldopentoses were used to prepare D-(I-¹³C)penturonic acids. Aqueous solutions of the I-¹³C-substituted penturonic acids, studied over a range of pH values by ¹³C-n.m.r. spectroscopy, were found to contain a- and b-furanoses, acyclic aldehyde and hydrate, and/or hydrated 2,5-lactone. The ratio of D-riburonic acid anomers was most sensitive to solution pH (a/b = 0.49 and 1.2 at pH 1.9 and 4.9, respectively). The values of the ¹H and ¹³C chemical shifts, and ¹H-¹H, ¹³C-¹H, and ¹³C-¹³C spin-coupling constants, were determined by ¹H-(300, 500, and 620 MHz) and ¹³C-(75 MHz) n.m.r. spectroscopy with the aid of 2-D ¹³C-¹H chemical shift correlation maps, 2-D ¹H-¹H COSY data, and ¹³C substitution, and were compared to those determined previously for structurally-related furanose rings. Isomerization of the penturonic acids at pH 5.0 and 50 °C gave the corresponding 4-pentulosonic acids.

Author(s): J. Barbat, J. Gelas and D. Horton
Title: Reactions of D-lyxose and D-xylose with 2-methoxypropene under kinetic conditions
Carbohydr. Res. Vol. 219, p. 115-121 (1991); ISSN: 0008-6215;


Abstract:
D-Lyxose (1) undergoes acetonation under kinetic conditions with 2-methoxypropene to give 2,3-O-isopropylidene-a-D-lyxofuranose (2) in high yield, further characterized as its 1,5-diacetate 3, thus affording a preparative route to 2. Forcing conditions are required to bring D-xylose (5) into reaction, leading to 39% of 3,5-O-isopropylidene-a-b-D-xylofuranose (7, further characterized as its 1,2-diacetate 9), 33% of 1,2:3,5-di-O-isopropylidene-a-D-xylofuranose (6), and 20% of 2,3:4,5-di-O-isopropylidene-aldehydo-D-xylose (8, further characterized as its aldehydrol diacetate 10). The results are all readily rationalized within the framework of the general principles earlier advanced for kinetic acetonation of sugars.

Author(s): J.P. Verheijden and P.J. Stoffyn
Title: Synthèse du 2,3-diméthyl-D-lyxose
Tetrahedron Vol. 1, No. 3, p. 253-258 (1957); ISSN: 0040-4020;


Abstract:
2,3-dimethyl-D-lyxose (VIII m.p. 116-117°) has been synthesised from lyxose according to "Schéma A" p. 254. and its structure confirmed by oxidation with periodic acid. The product obtained by degradation of 3,4-galactosamine with ninhydrin has been shown to be indistinguishable, by paper chromatography, from synthetic 2,3-dimethyl-D-lyxose.

Author(s): S.A. Abbas, A.H. Haines and A.G. Wells
Title: Synthesis of 2,4-Di-O-methyl-D-lyxose
Carbohydr. Res. Vol. 42, No. 2, p. 362-364 (1975); ISSN: 0008-6215;

Author(s): P.R. Sundararajan and V.S.R. Rao
Title: Theoretical studies on the conformation of aldopyranoses
Tetrahedron Vol. 24, No. 1, p. 289-295 (1968); ISSN: 0040-4020;


Abstract:
The potential energy of non-bonded interactions for sixteen aldoheopyranoses and eight aldopentopyranoses have been calculated using the Kitaigorodsky type functions. It has been shown that the C₁ (chair) conformation has the lowest energy for all the aldohexoses and most aldopentoses. Only for a-D-arabinose and a-D-ribose does the 1C conformation have the lowest energy. The energy difference between C₁ and ¹C conformations of b-D-arabinose and a-D-lyxose is small and it is likely that these molecules exist in C₁[larr2] equilibrium. The differences in the preferred conformations assigned by the earlier instability schemes and the present energy calculations are also discussed.

Author(s): H. Zinner, B. Richard, M. Blessman and M. Schlutt
Title: Derivate der Zucker-thioacetale; XXXVII. Mitteilung. Benzyliden-verbindungen der pentose-dialkylacetale
Carbohydr. Res. Vol. 2, No. 3, p. 197-203 (1966); ISSN: 0008-6215;


Abstract:
The rules of Hann and Hudson apply not only to the formation of benzylidene derivatives of sugar alcohols and pentose dithioacetals, but also to the formation of di-O-benzylidenepentose dialkyl acetals. Treatment of the dimethyl acetals of D-ribose, D-xylose, and D-lyxose with benzaldehyde and zinc chloride yields 2,4:3,5-di-O-benzylidene derivatives. D-Arabinose dimethyl acetal gives a 2,3:4,5-di-O-benzylidene derivative. The structures of these compounds were proved by their synthesis from the appropriate di-O-benzylidenepentose diethyl dithioacetals.
Zusammenfassung:
Die Regeln von Hann and Hudson haben nicht nur Gültigkeit für die Bildung von Benzyliden-Verbindungen der Zuckeralkohole and Pentose-thioacetale, sondern auch für die Bildung der Di-O-benzyliden-pentose-dialkylacetale. Bei der Umsetzung von Dimethylacetalen der D-Ribose, D-Xylose, and D-Lyxose mit Benzaldehyd bei Gegenwart von Zinkchlorid erhält man 2,4:3,5-Di-O-benzyliden-Verbindungen. Das D-Arabinose-dimethylacetal liefert ein 2,3:4,5-Di-O-benzyliden-Derivat. Die Struktur der Verbindungen wird durch Synthesen aus zugehörigen Di-O-benzyliden-pentosediäthylthioacetalen bewiesen.

Author(s): D. Horton and J. D. Wander
Title: Conformation of acyclic derivatives of sugars
. Part VI. Conformations of aldehydo-aldose peracetates in solution
Carbohydr. Res. Vol. 15, No. 2, p. 271-284 (1970); ISSN: 0008-6215;


Abstract:
2,3,4,5-Tetra-O-acetyl-aldehydo-D-ribose (1), its D-arabino (2), D-xylo (3), and D-lyxo (4) analogs, and 2,3,4,5-tetra-O-acetyl-6-deoxy-aldehydo-D-galactose (5) have been studied in chloroform-d solution by n.m.r. spectroscopy at 100 MHz. Signals of all protons were assigned, and verified by spin decoupling, and first-order coupling-constants were determined. The favored conformation of these compounds was shown to be the extended, planar, zigzag form 2, except when such a conformation would lead to an eclipsed, 1,3-interaction between pairs of substituents, in which case the favored conformation is a "sickle" form3¯5 in which the 1,3-interaction is alleviated, by rotation about a carbon-carbon bond of the chain, to give a different rotameric state. The diphenyl dithioacetals (8 and 9, respectively) of 2,3,4,5-tetra-O-acetyl--D-lyxose and 2,3,4,5-tetra-O-acetyl-6-deoxy-D-mannose were prepared, and their conformations studied; demercaptalation of these compounds by mercuric chloride proved to be more difficult than with the diethyl analogs.

Author(s): H. Kuzuhara, H. Hiroyuki Terayama, H. Ohrui and S. Sakae Emoto
Title: Preparation of D-lyxose and some of its furanose derivatives
Carbohydr. Res. Vol. 20, No. 1, p. 165-169 (1971); ISSN: 0008-6215;

keywords: 1,2-O-isopropylidene-b-D-lyxofuranose; 3-O-benzyl-1,2-O-isopropylidene-b-D-lyxofuranose

Author(s): H.S. Isbell, H.L. Frush and E.T. Martin
Title: Reactions of carbohydrates with hydroperoxides. Part I. Oxidation of aldoses with sodium peroxide
Carbohydr. Res. Vol. 26, No. 2, p. 287-295 (1973); ISSN: 0008-6215;


Abstract:
It was found that aqueous alkaline hydrogen peroxide solutions at 0° degrade aldohexoses almost quantitatively to 6 moles of formic acid, and aldopentoses to 5 moles. A mechanism is proposed for the stepwise degradation of aldoses to formic acid, consisting of the addition of a hydroperoxide anion to the aldehydo modification of the sugar, followed by decomposition of the adduct to formic acid and the next lower aldose. The authors found that iron salts accelerate the reaction and suggested that decomposition of the peroxide adduct may take place by a free-radical process, as well as by an ionic mechanism. Reactions of the following hexoses were measured: D-glucose, D-mannose, D-galactose, D-allose, D-altrose, and D-talose, and the following pentoses: D-xylose, D-arabinose, D-lyxose, and D-ribose. The reaction rates for the various sugars increased in the order just cited.

Author(s): T.A. Giudici and J.S. Griffin
Title: The interconversion of monosaccharide configurations: Labinose to lyxose
Carbohydr. Res. Vol. 33, No. 2, p. 287-295 (1974); ISSN: 0008-6215;


Abstract:
Selective oxidation of the primary hydroxyl group of 1,3-O-benzylidene-D-arabinitol (1) with methyl sulfoxide-N,N'-dicyclohexylcarbodiimide-pyridinium trifluoroacetate (Pfitzner-Moffatt reagent), followed by debenzylidenation, provided a route for configurational conversion of D-arabinose into D-lyxose (4). The same reaction-sequence was then used for the synthesis of the enantiomers. The sugars prepared were purified by ion-exchange column chromatography and characterized by o.r.d., n.m.r., t.l.c., and g.l.c.

Author(s): D. Horton and S.G. Kokrady
Title: Acyclic-sugar nucleoside analogs derived from cytosine with the D-aldopentoses, and from uracil with D-lyxose and D-ribose
Carbohydr. Res. Vol. 80, No. 2, p. 364-374 (1980); ISSN: 0008-6215;

Author(s): G.E. Taylor and J.M. Waters
Title: The structure of a compound of unexpected conformation involved in the xylose-lyxose epimerization
Tetrahedron Lett. Vol. 22, No. 133, p. 1277-1278 (1981); ISSN: 0040-4039;


Abstract:
The structure of a molybdenum(VI) complex of the sugar, lyxose, has been established by the X-ray method.

Author(s): V. Boucheza, I. Stasika, D. Beaupère and R. Uzana
Title: Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives
Carbohydr. Res. Vol. 300, No. 2, p. 139-142 (1997); ISSN: 0008-6215;

keywords: pentono-1,4-lactones; thionyl chloride; thionyl bromide; dimethyl formamide; regioselective halogenation; 5-chloro-5-deoxy-pentono-1,4-lactone; 5-bromo-5-deoxy-pentono-1,4-lactone
Abstract:
Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds.

Author(s): O. Varelaa, P.A. Zunszaina, D.O. Ciceroa, R.F. Baggiob, D.R. Vegab and M.T. Garlandc
Title: Conformation of 4-thio-D-lyxono-1,4-lactone in solution and in the crystalline state
Carbohydr. Res. Vol. 280, No. 2, p. 187-196 (1996); ISSN: 0008-6215;

keywords: Aldopentono-1,4-thiolactone conformation; Heteronuclear ¹³C-¹H coupling constants; 2D NMR heteronucleus-coupled H-H correlation (HETLOC)
Abstract:
The conformation in 2H₂O of 4-thio-D-lyxono-1,4-lactone (1) was studied by nuclear magnetic resonance spectroscopy, by means of homonuclear (J1H,1H) and heteronuclear (J1H,13C) coupling constants. The couplings were directly measured by a two-dimensional heteronucleus-coupled 1 hetero-half-filtered proton-proton correlation (HETLOC) experiment, which does not require 13C isotopic enrichment. In solution, the thiolactone ring of 1 adopts preferentially the E3 conformation, and its hydroxymethyl group populates mainly the gt rotamer. The X-ray diffraction data of a single crystal of 1 indicates that also in the solid state the thiolactone ring adopts an E3 conformation, with a puckering somewhat larger than that observed for aldono-1,4-lactones and furanose rings. The molecules are linked by hydrogen bonds, which form chains. Particularly, O-5 is fully engaged as donor and acceptor in hydrogen bonding and the rotameric conformation of the hydroxymethyl group of 1 is fixed in the tg form.

Author(s): K. Bock, I. Lundt and C. Pedersen
Title: The preparation of some bromodeoxy- and dibromodideoxy-pentonolactones. Reaction of Aldonic Acids with Hydrogen Bromide, Part IV.
Carbohydr. Res. Vol. 104, No. 1, p. 79-85 (1982); ISSN: 0008-6215;


Abstract:
Treatment of ammonium D-xylonate with hydrogen bromide in acetic acid yields 2,5-dibromo-2,5-dideoxy-D-lyxono-1,4-lactone (2a), whereas similar treatment of potassium D-arabinonate gives 5-bromo-5-deoxy-D-arabinono-1,4-lactone (8a) as the main product. Two isomeric 2,5-dibromo-2,5-dideoxy-1,4-lactones are also formed in minor amounts. Selective hydrogenolysis of (2a) affords 5-bromo-2,5-dideoxy-D-threo-pentono-1,4-lactone, while prolonged treatment results in the formation of 3-hydroxypentanoic acid. Similarly, hydrogenolysis of (8a) produces a 2,3-dihydroxypentanoic acid together with smaller amounts of 5-deoxy-D-arabinono-1,4-lactone; the latter also results from hydrogenolysis of 5-deoxy-5-iodo-D-arabinono-1,4-lactone with Raney nickel.

Author(s): K. Bock, I. Lundt and C. Pedersen
Title: The preparation of some bromodeoxy- and dibromodideoxy-pentonolactones. Reaction of Aldonic Acids with Hydrogen Bromide, Part III.
Carbohydr. Res. Vol. 90, No. 1, p. 17-26 (1981); ISSN: 0008-6215;


Abstract:
Brief reaction of D-lyxono-1,4-lactone (1) with hydrogen bromide in acetic acid (HBA) yields 2-bromo-2-deoxy-D-xylono-1,4-lactone (2), and a similar treatment of D-ribono-1,4-lactone (8) gives 2-bromo-2-deoxy-D-arabinono-1,4-lactone (12). On longer reaction with HBA, 1 is converted into 2,5-dibromo-2,5-dideoxy-D-xylono-1,4-lactone, whereas 8 forms a mixture of 2,5-dibromolactones. Reduction of 2 and 12 gives 2-bromo-2-deoxy-D-xylose and -D-arabinose, respectively. On hydrogenolysis, (2) and (12) are converted into 2-deoxy-a-threo- and -b-2-deoxy-D-erythro-pentono-1,4-lactone, respectively. The 2,5-dibromolactones can be selectively hydrogenolysed to 5-bromo-2,5-dideoxy-D-pentono-1,4-lactones.

Author(s): P. Dauban, B. Hofmann and R.H. Dodd
Title: Synthesis of 2,3-aziridino-2,3-dideoxy-D-lyxono-g-lactone 5-phosphonate from D-ribose, a new member of the 2,3-aziridino-g-lactone family of synthons
Tetrahedron Vol. 53, No. 31, p. 10743-10752 (1997); ISSN: 0040-4020;


Abstract:
A formal synthesis of the novel (1S,4S,5R)-N-(benzyloxycarbonyl)-4-(diethoxyphosphinyl)methyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 4 from D-ribose is presented. A key step involves the use of the 2,3-sulfate 12 for introduction of the C-3 azide functionality prior to aziridine ring formation.

Author(s): Y. Wanga, G.W.J. Fleet and L. Zhaoa
Title: 1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl (TIPS) migration facilitates one-pot formation of enantiomerically pure methyl 2,3-epoxy-D-xylonate
Carbohydr. Res. Vol. 307, No. 1-2, p. 159-162 (1998); ISSN: 0008-6215;

keywords: TIPS; Migration; Methyl 2,3-epoxy-D-xylonate; D-Lyxono-1,4-lactone; epoxyester; 5-O-1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl-D-lyxono-1,4-lactone; 3,5-O-(1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone; Methyl 2,3-anhydro-4,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-xylonate; 2,3-Anhydro-4,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-xylitol; Methyl 2,3-anhydro-D-xylonate; Silyl-Wanderung; Wanderung einer Silylschutzgruppe
Abstract:
The reaction of 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-D-lyxono-1,4-lactone with K₂CO₃ in dry methanol at -10 °C gave enantiomerically pure methyl 2,3-anhydro-4,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-xylonate as the single product, resulting from migration of the TIPS group in an alkoxide intermediate.

Author(s): M.S. Wolfe, D.R. David R. Borcherding and R.T. Borchardt
Title: A 9-step enantiospecific synthesis of (-)-aristeromycin from D-ribonic acid g-lactone
Tetrahedron Lett. Vol. 30, No. 12, p. 1453-1456 (1989); ISSN: 0040-4039;


Abstract:
A short, efficient, enantiospecific total synthesis of (-)-aristeromycin, which can be modified for making analogues of this carbocyclic nucleoside, is reported.

Author(s): M.-I. Lim and V.E. Marquez
Title: Total synthesis of (-)-neplanocin A
Tetrahedron Lett. Vol. 24, No. 50, p. 5559-5562 (1983); ISSN: 0040-4039;


Abstract:
A total synthesis of (-)-neplanocin A has been accomplished in 15 steps starting from the readily available D-(+)-ribonic acid-g-lactone.

Author(s): M.-I. Lim and V.E. Marquez
Title: A synthetic approach towards neplanocin A: Preparation of the optically active cyclopentene moiety from D-ribose
Tetrahedron Lett. Vol. 24, No. 38, p. 4051-4054 (1983); ISSN: 0040-4039;


Abstract:
D-(-)-ribose has been converted to the chiral 2-cyclopenten-1-one derivative which has the correct stereochemistry and appropriate functionalities for the construction of neplanocin A.

Author(s): M. Arita, T. Okumoto, T. Saito, Y. Hoshino, K. Fukukawa, S. Shuto, M. Tsujino, H. Sakakibara and M. Ohno
Title: Enantioselective synthesis of new analogs of neplanocin A and their biological activity
Carbohydr. Res. Vol. 171, No. 1, p. 233-258 (1987); ISSN: 0008-6215;


Abstract:
Various carbocyclic nucleosides analogs of neplanocin A (such as 5-aminoimidazole-4-carboxamide riboside, uridine, 5-iodouridine, 4-thiouridine, cytidine, thymidine, 2'-deoxyguanosine, ribofuranosylthymine, a 2,2'-anhydroderivative, 2'-deoxycytidine, 2'-deoxythiouridine, and a-arabinofuranosylcytosine analogs) were synthesized from (1R, 2S, 3R)-2,3-isopropylidenedioxy-4-methoxymethyloxymethyl-4-cyclopentenylamine. The cytidine analog was found the most active in inhibiting mouse lymphoma L5178Y cells in vitro at a concentration as low as 0.8 mg/mL.

Author(s): M. Bodenteich and V.E. Marquez
Title: Total synthesis of (±)-neplanocin F
Tetrahedron Lett. Vol. 30, No. 37, p. 4909-4912 (1989); ISSN: 0040-4039;


Abstract:
(±)-Neplanocin F was synthesized in 12 steps from the racemate (3/4), which was available from D-ribonolactone.

Author(s): L.S. Jeong, G. Buenger, J.J. McCormack, D.A. Cooney, Z. Hao and V.E. Marquez
Title: Carbocyclic Analogues of the Potent Cytidine Deaminase Inhibitor 1-(b-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one (Zebularine)
J. Med. Chem. Vol. 41, No. 14, p. 2572-2578 (1998); ISSN: 0022-2623;


Abstract:
Three carbocyclic analogues of the potent cytidine deaminase inhibitor (CDA) zebularine were synthesized. The selected pseudosugar templates correspond, respectively, to the cyclopentenyl moiety of neplanocin A (compound 4), the cyclopentyl moiety of aristeromycin (compound 5), and a newly designed, rigid bicyclo[3.1.0]hexane moiety (compound 6). These three carba-nucleoside versions of zebularine were fashioned to overcome the inherent instability of the parent drug. Each target compound was approached differently using either convergent or linear approaches. The immediate precursor to the cyclopentenyl analogue 4 was obtained by a Mitsunobu coupling of pseudosugar 7 with 2-hydroxypyrimidine. The cyclopentyl analogue 5 was linearly constructed from carbocyclic amine 17, and the final target 6 was similarly constructed from the carbobicyclic amine 27. Of the three target compounds, only 5 showed a significant level of inhibition against human CDA, but it was 16 times less potent than zebularine (Ki = 38 mM vs Ki(apparent) = 2.3 mM). Although these carbocyclic analogues appeared to be more stable than zebularine, replacement of the electronegative CO4' oxygen for the less electronegative carbon in 4-6 presumably reduces the capacity of the pyrimidin-2(1H)-one ring to form a covalent hydrate, a step considered crucial for the compound to function as a transition-state inhibitor of the enzyme.

Author(s): K. Hirota, Y. Monguchi, Y. Kitade and H. Sajiki
Title: Ribofuranose-ring Cleavage of Purine Nucleosides with Diisobutylaluminum Hydride: Convenient Method for the Preparation of Purine Acyclonucleosides
Tetrahedron Vol. 53, No. 49, p. 16683-16698 (1997); ISSN: 0040-4020;


Abstract:
The reaction of 2',3'-O-isopropylidene protected purine nucleosides with diisobutylaluminum hydride (DIBAL-H) caused the reductive cleavage of the C-1'-O-4' bond to give the corresponding 9--ribitylpurines. The ring cleavage of inosine 1a, thioinosine 1f, and their derivatives having an alkyl group at the O⁶- or S⁶- position 1c, e, and g proceeded smoothly to afford the corresponding ribityl derivatives 2a, f, c, e, and g, whereas whereas N6-methylated adenosine derivatives 1k and 1 remarkably resisted the DIBAL-H reduction. 5'-Deoxy and 5'-chloro-5'-deoxy derivatives 1b, d, i, and j also underwent reductive cleavage at the sugar moiety under similar conditions. An acyclic analog of guanosine 6, which is of biological interest, was prepared from a guanosine derivative 5 in a similar way. The present methodology for the synthesis of purine acyclonuculeosides was also applied to the preparation of an acyclic analog 17 of neplanocin A.

Author(s): K. Kato, H. Hayakawa, H. Tanaka, H. Kumamoto, S. Shindoh et al.
Title: A New Entry to 2-Substituted Purine Nucleosides based on Lithiation-Mediated Stanny Transfer of 6-Chloropurine Nucleosides
J. Org. Chem. Vol. 62, No. 20, p. 6833-6841 (1997); ISSN: 0022-3263;


Abstract:
In spite of exclusive lithiation at the 8-position of 9-(2,3,5-tris-O-TBDMS-b-D-ribofuranosyl)-6-chloropurine (2) with LDA, subsequent quenching of its lithiated species with Bu3SnCl (or TMSCl) results in the formation of 2-substituted products. Under optimized reaction conditions, where LTMP was used as a lithiating agent, 9-(2,3,5-tris-O-TBDMS-b-D-ribofuranosyl)-6-chloro-2-(tributylstannyl)purine (11) was formed in quantitative yield. Several experiments carried out to verify the reaction mechanism suggested that an anionic stannyl (or silyl) transfer from the 8- to the 2-position had been involved. Manipulation of the 2-tributylstannyl group in 11 and its adenine counterpart (22) has disclosed a new entry to 2-substituted purine nucleosides. This chemistry was briefly applied to the synthesis of the 2-fluoro analogue of neplanocin A.

Author(s): A. Matsuda, H. Kosaki, Y. Yoshimura, S. Shuto, N. Ashida, K. Konno and S. Shigeta
Title: Nucleosides and nucleotides. 142. An alternative synthesis of 9-(5,6-dideoxy-b-D-ribo-hex-5-ynofuranosyl) adenine and its antiviral activity
Bioorg. Med. Chem. Lett. Vol. 5, No. 15, p. 1685-1688 (1995); ISSN: 0960-894X;


Abstract:
An alternative synthesis of 9-(5,6-dideoxy-b-D-ribo-hex-5-ynofuranosyl)adenine (5), which is known to be a potent, irreversible, and time-dependent inhibitor of AdoHcy hydrolase, has been accomplished. Compound5 had a potent antiviral activity against influenza A and B viruses as well as vesicular stomatitis virus. Since the usual inhibitors of AdoHcy hydrolase, such as neplanocin A, are inactive on both influenza viruses, the mechanism of action of 5 would be different from that of known AdoHcy hydrolase inhibitors.

Author(s): S. Ohira, T. Sawamoto and M. Yamato
Title: Synthesis of (-)-Neplanocin A via C-H Insertion of Alkylidenecarbene
Tetrahedron Lett. Vol. 36, No. 9, p. 1537-1538 (1995); ISSN: 0040-4039;


Abstract:
(-)-Neplanocin A, a naturally occurring carbocyclic nucleoside was synthesized via C-H insertion reaction of the alkylidenecarbene, which was generated by the reaction of lithiotrimethylsilyldiazomethane and the ketone derived from D-ribose.

Author(s): Takumi Obara, Yoshinori Kosugi, Yasuyoshi Saito, Minoru Toriya, Satoshi Yaginuma, Shiro Shigeta and Akira Matsuda Satoshi Shuto
Title: New neplanocin analogues. III. 6'R-configuration is essential for the antiviral activity of 6'-C-methyl-3-deazaneplanocin A's
Bioorg Med. Chem. Lett. Vol. 4, No. 4, p. 605-608 (1994); ISSN: 0960-894X;


Abstract:
(6'R)- and (6'S-6'-C-methyl-3-deazaneplanocin A's were synthesized from D-ribose as anti-RNA virus agents. Of these compounds, (6'R)-6'-C-methyl-3-deazaneplanocin A (4b) showed the greatest anti-RNA virus activity in vitro. It was found that the 6'R-configuration was essential for the antiviral activity of 6'-C-methylneplanocin A derivatives.

Author(s): S. Hanessian, R. Léger and M. Alpegiani
Title: Free radical-induced C-allylation of a-bromolactones. Synthesis of 2-C-allyl-2-deoxy-D-arabino-and -D-ribono-1,4-lactones
Carbohydr. Res. Vol. 228, No. 1, p. 145-155 (1992); ISSN: 0008-6215;

Author(s): Y. Kinoshita, J.R. Ruble and G.A. Jeffrey
Title: The crystal structure of D-ribono-1,4-lactone at -150°
Carbohydr. Res. Vol. 92, No. 1, p. 1-7 (1981); ISSN: 0008-6215;

Author(s): S. Signorella, S. Garcia and L.F. Sala
Title: Degradative oxidation of D-ribono-1,4-lactone by Cr(VI) in perchloric acid
Polyhedron Vol. 16, No. 4, p. 701-706 (1997); ISSN: 0277-5387;

keywords: ribonolactone; chromium; oxidation; kinetics; mechanism; Cr(V); Cr(VI)
Abstract:
The oxidation of D-ribono-1,4-lactone by Cr(VI) yielded D-erythronic acid, erythrose, carbon dioxide and Cr(III) as final products when a 15-fold or higher excess of sugar over Cr(VI) was used. The kinetics of the redox processes involving the Cr(VI)/Cr(III) couple were determined and a mechanism is proposed. The complete rate law for the Cr(VI) oxidation reaction is expressed by: -d[Cr(VI)]/dt = {a[S] +b [S][H+] + c[H+]3} [Cr(VI)]T, where a = 3.09 × 10-3 M-1 s-1, b = 4.98 × 10-2 M-2 s-1, c = 1.07 × 10-3 M-3 s-1 and S refers to the total reductant concentration, at 60 °C. Cr(V) is formed in a fast step by reaction of the CO-2 radical and Cr(VI), and Cr(V) reacts with the organic substrate faster than Cr(VI) does. The EPR spectra show that the intermediate Cr(V) complex (g = 1.978) is formed and decays by a first-order process.

Author(s): D.H.R. Barton, J. Camara, X. Cheng, S.D. Géro, J.C. Jaszberenyi and B. Quiclet-Sire
Title: From Cabohydrates to Carbocycles: radical routes via tellurium derivatives
Tetrahedron Vol. 48, No. 42, p. 9261-9276 (1992); ISSN: 0040-4020;

keywords: Ketalisierung /Acetalisierung von Ribose; D-Ribono-1,4-lacton; Ketalisierung von D-Ribonsäure-g-lacton; 2,3-O-Isopropyliden-D-ribose; 2,3-O-Isopropyliden-D-ribono-1,4-lacton; radikalische Cyclisierung; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopenten-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopenten-1-on; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopenten-1-on; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopenten-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropylidencyclopent-2-en-1-on; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropylidencyclopent-4-en-1-on; (2S,3S)-2,3-Isopropylidendioxycyclopent-4-en-1-on; (4S,5S)-4,5-Isopropylidendioxycyclopent-2-en-1-on; (4S,5S)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopentenon; (2S,3S)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopentenon; (2S,3S)-2,3-Isopropylidendioxy-4-cyclopentenon; (4S,5S)-4,5-Isopropylidendioxy-2-cyclopentenon; (4R,5R)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopenten-1-on; (2R,3R)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopenten-1-on; (2R,3R)-2,3-Isopropylidendioxy-4-cyclopenten-1-on; (4R,5R)-4,5-Isopropylidendioxy-2-cyclopenten-1-on; (4R,5R)-4,5-Dihydroxy-4,5-O-isopropylidencyclopent-2-en-1-on; (2R,3R)-2,3-Dihydroxy-2,3-O-isopropylidencyclopent-4-en-1-on; (2R,3R)-2,3-Isopropylidendioxycyclopent-4-en-1-on; (4R,5R)-4,5-Isopropylidendioxycyclopent-2-en-1-on; (4R,5R)-4,5-Dihydroxy-4,5-O-isopropyliden-2-cyclopentenon; (2R,3R)-2,3-Dihydroxy-2,3-O-isopropyliden-4-cyclopentenon; (2R,3R)-2,3-Isopropylidendioxy-4-cyclopentenon; (4R,5R)-4,5-Isopropylidendioxy-2-cyclopentenon

Author(s): A. Klemer and M. Kohla
Title: Einstufige stereoselekive Synthesen von Cyclopenanol-Derivaten aus 1,5-Anhydro-2,3-O-benzyliden-b-D-Ribofuranose
Liebigs Ann. Chem., p. 683-686 (1987); ISSN: 0170-2041;

keywords: Baldwin-Regeln

Author(s): J. Gelas and D. Horton
Title: Acetonation of D-ribose and D-arabinose with alkyl isopropenyl ethers
Carbohydr. Res. Vol. 45, p. 181-195 (1971); ISSN: 0008-6215;

keywords: ketalization /acetalisation using kinetically controlled conditions; ethyl isopropenylether; methyl isopropenylether; 3,4-O-isopropyliden-D-ribopyranose; 2,3-O-isopropyliden-D-ribofuranose; ketalization of D-ribose; D-arabinose; 3,4-O-isopropyliden-b-D-arabinopyranose; 1,2; 3,4-Di-O-isopropyliden-b-D-arabinopyranose

Author(s): J.K.N. Jones, P.W. Kent and M. Stacey
Title: Synthesis of some derivatives of D- and L-Arabinose
J. Chem. Soc., p. 1341-1344 (1947);

keywords: ketalization of arabinose with cupric sulfate /barium carbonate in acetone; oxidation of calcium-D-gluconat with hydrogen peroxide in the presence of iron acetate; oxidation of sugars; oxidation of carbohydrates with hydrogen peroxide; acetalization of L-arabinose with cupric sulfate and cupric sulfate-sulfuric acid; 3,4-O-isopropylidene-L-arabinose; 1,2; 3,4-Di-O-isopropyliden-L-arabinose

Author(s): E. Vis and H.G., jr. Fletcher
Title: 1,5-Anhydro-b-D-ribofuranose and the "Monoacetone Anhydroribose" of Levene and Stiller
J. Am. Chem. Soc. Vol. 79, p. 1182-1185 (1957); ISSN: 0002-7863;

keywords: 2,3-O-Isopropyliden-b-D-ribofuranose; 2,3-O-Benzyliden-b-D-ribofuranose; 1,5-Anhydro-b-D-ribofuranose

Author(s): H. Ohle and G. Berend
Title: Über die Aceton-Verbindungen der Zucker and ihre Derivate. VIII: Eine neue Mono-aceton-L-Arabinose
Chem. Ber. Vol. 60, p. 810-811 (1927);

keywords: Acetalisierung von L-Arabinose mit Kupfersulfat; 3,4-O-Isopropyliden-L-arabinose

Author(s): T.B. Grindley and V. Gulasekharam
Title: Benzylidene acetal structural elucidation by NMR spectroscopy: application of carbon-13 NMR-spectral parameters
Carbohydr. Res. Vol. 74, p. 7-30 (1979); ISSN: 0008-6215;

keywords: ketalization of ribose and arabinose with benzaldehyde; acetalization of L-arabinose with benzaldehyde; O-benzylidene-derivatives of ribose and arabinose; chemical NMR-assigments of the acetalic-carbon atom for detection of the formation of a pyranose or furanose ring

Author(s): S. Jacobsen and C. Pedersen
Title: Dioxolanylium ions derived from Carbohydrates. I. Reactions with water and with bromide ions
Acta Chem. Scand. B Vol. 28B, p. 866-872 (1974); ISSN: 0302-4369;

keywords: methyl 3,4-O-benzylidene-b-D-arabinopyranoside; methyl 2,3-O-benzylidene-a-D-arabinopyranoside; 2,3-O-benzylidene-b-D-ribopyranoside

Author(s): H. Ovaa, J.D.C. Codee, B. Lastdrager, H.S. Overkleeft, G.A. van der Marel and J.H. van Boom
Title: A stereoselective and efficient route to (3S,4R,5S)-(+)-4,5-dihydroxy-cyclopent-1-en-3-ylamine: The side chain of the hypermodified nucleoside Q
Tetrahedron Lett. Vol. 39, p. 7987-7990 (1998); ISSN: 0040-4039;

keywords: Carbanucleoside; Grubbs-Katalysator; Ringbildungs-Metathese; Olefin-Metathese; 4,5-dihydroxy-2-cyclopenten-1-one; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-ene-1-one; Ringbildungs-Metathese; 4,5-O-Isopropyliden-4,5-dihydroxycyclopent-2-en-1-ol; 2,3-O-Isopropyliden-2,3-dihydroxycyclopent-4-en-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-ene-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-on; 4,5-O-Isopropylidenecyclopent-2-ene-4,5-diol-1-one; 4,5-O-Isopropyliden-2-cyclopenten-4,5-diol-1-one

Author(s): M. Ono, K. Nishimura, H. Tsubouchi, Y. Nagaoka and K. Tomioka
Title: Total synthesis of (-)-Neplanocin A by using Lithium Thiolate-initiated Michael-Aldol Tandem cyclization reaction
J. Org. Chem. Vol. 66, p. 8199-8203 (2001); ISSN: 0022-3263;

keywords: Neplanocin A; Carbanucleoside; (R,R)-2,3-O-Isopropylidene-threitol; (R,R)-2,3-O-Isopropylidenedioxy-1,4-butanediol; (R,R)-2,3-O-Isopropylidendioxy-1,4-butandiol

Author(s): M.K. Gurjar and K. Maheshwar
Title: Stereoselective synthesis of a novel carbocyclic Nucleoside
J. Org. Chem. Vol. 66, p. 7552-7554 (2001); ISSN: 0022-3263;

keywords: 1,2; 5,6-Di-O-isopropylidene-R-D-gluco-furanose; Grubb´s Katalysator; Metathese; Carbanucleoside; Neplanocin A; Aristeromycin

Author(s): F. Fazio and M.P. Schneider
Title: A facile access to 2-deoxy-L-ribose
Tetrahedron: Asymmetry Vol. 12, No. 15, p. 2143-2145 (2001); ISSN: 0957-4166;

Author(s): T. Sambaiah, P.E. Fanwick and M. Cushman
Title: Investigation of an unexpected addition reaction that occurs when 2,3:4,5-Di-O-isopropylidene-D-ribose diethyl Dithioacetal is treated with Mercuric Oxide and Mercuric Chloride
J. Org. Chem. Vol. 66, p. 4405-4408 (2001); ISSN: 0022-3263;

Author(s): N. Gathergood, K.R. Knudsen and K.A. Jørgensen
Title: Enantioselective synthesis of optically active carbocyclic sugars
J. Org. Chem. Vol. 66, p. 1014-1017 (2001); ISSN: 0022-3263;

keywords: Carbanucleoside; carbocyclische Zuckerderivate; Osmylierung mit Osmiumtetroxid

Author(s): S. Cicchi, M. Corsi, A. Brandi and A. Goti
Title: Straight forward synthesis of enantiomerically pure (3S,4R)- and (3R,4S)-3,4-Isopropylidenedioxypyrroline 1-oxide, precursors of functionalized cis-Dihydroxy azaheterocycles, by a novel “one-Pot” procedure
J. Org. Chem. Vol. 67, p. 1678-1681 (2002); ISSN: 0022-3263;

keywords: L-Arabinose; D-Arabinose; L-Erythrose; D-Erythrose; D-Isoascorbinsäure; D-isoascorbic acid; Erythronolactol; D-Erythrose; 2,3-O-Isopropylidene-D-erythronolacton; 2,3-O-Isopropyliden-D-erythronolacton; 2,3-O-Isopropylidene-D-erythrose; meso-2,3-O-Isopropylidene-erthritiol; 2,3-O-Isopropylidenbutan-1,2,3,4-tetrol
Abstract:
The enantiomerically pure nitrone (3), avaluable precursor of mono- and bicyclic azaheterocycles, has been synthesized in 57 % yield by a novel “one-pot” process starting from lactol (1), in turn readily available from D-arabinose. The same process, consisting of reaction with a O-silyl-protected hydroxylamine followed by mesylation in pyridine, furnished ent-3 in 55 % yield when applied to L-arabinose.

Author(s): S. Zhao, L. Petrus and A.S. Serianni
Title: 1-Deoxy-D-xylulose: Synthesis based on Molybdate-catalysed rearrangement of a brached-chain Aldotetrose
Org. Lett. Vol. 3, No. 24, p. 3819-3822 (2001);

keywords: D-Erythronolacton; D-Erythrose; Reduktion von D-Erythronolacton mit Natriumborhydrid bei ph 4-7 zu D-Erythrose; 2,3-O-Isopropylidene-D-erythrose; 2,3-O-Isopropylidene-D-erythronolacton; 2,3-O-Isopropyliden-D-erythrose; 2,3-O-Isopropyliden-D-erythronolacton

Author(s): D.H. Shin, H.W. Lee, S.S. Park, J.H. Kim, L.S. Jeong and M.W. Chun
Title: Synthesis of (-)-Neplanocin A analogues as potential antiviral agents
Arch. Pharm. Res. Vol. 23, No. 4, p. 302-309 (2000);

keywords: Neplanocin A; Nucleoside; Carbanucleoside; antivirale Mittel

Author(s): M.E.B. Smith, M.C. Lloyd, N. Derrien, R.C. Lloyd, S.J.C. Taylor, D.A. Chaplin, G. Casy and R. McCague
Title: An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery
Tetrahedron: Asymmetry Vol. 12, p. 703-705 (2001); ISSN: 0957-4166;

keywords: Carbanucleoside; 3-Amino-4-hydroxycyclopentan-1-carbonsäure

Author(s): L.E. Martínez, W.A. Nugent and E.N. Jacobsen
Title: Highly efficient and enantioselective synthesis of carbocyclic Nucleoside analogs using selective early transition metal catalysis
J. Org. Chem. Vol. 61, No. 22, p. 7963-7966 (1996); ISSN: 0022-3263;

keywords: Aristeromycin; ring-closing-methathesis; olefin-metathese; ringbildungs-metathese; Alternative zu Grubbs-Katalysator; Jacobsen-Katalysator; kinetisch-hydrolytische Racematspaltung mit Chrom(salen)-Komplex; selektive Esterreduktion mit LAH ohne Epoxidöffnung; Aminocyclopentanole; Carbanucleoside

Author(s): A. Blaser and J.-L. Reymond
Title: A selective a-L-Fucosidase Inhibitor based on an aminocyclopentane framework
Helv. Chim. Acta Vol. 82, p. 760-768 (1999); ISSN: 0018-019X;

keywords: Carbanucleoside; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-ene-1-one; Epoxidierung von 4,5-O-Isopropyliden-4,5-dihydroxycyclopent-2-en-1-on; 2,3-O-Isopropyliden-2,3-dihydroxycyclopent-4-en-1-on; 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-one; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-eneone-(1); 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-on; 4,5-O-Isopropylidenecyclopent-2-ene-4,5-diol-1-one; 4,5-O-Isopropyliden-2-cyclopenten-4,5-diol-1-one

Author(s): H. Ovaa, J.D.C. Codée, B. Lastdrager, H.S. Overkleeft, G.A. van der Marcel and J.H. van Boom
Title: A versatile approach to the synthesis of highly functionalised Carbocycles
Tetrahedron Lett. Vol. 40, p. 5063-5066 (1999); ISSN: 0040-4039;

keywords: Carbanucleoside; Grubbs-Katalysator; Olefin-Metathese; Ringbildungs-Metathese; 4,5-dihydroxy-2-cyclopenten-1-one; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-ene-1-one; Ringbildungs-Metathese; 4,5-O-Isopropyliden-4,5-dihydroxycyclopent-2-en-1-ol; 2,3-O-Isopropyliden-2,3-dihydroxycyclopent-4-en-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxycyclopent-2-ene-1-ol; 4,5-O-Isopropylidene-4,5-dihydroxy-2-cyclopentene-1-on; 4,5-O-Isopropylidenecyclopent-2-ene-4,5-diol-1-one; 4,5-O-Isopropyliden-2-cyclopenten-4,5-diol-1-one
Vergleiche Choi, W.J.; Park, J.G.; Yoo, S.J.; Kim, H.O.; Moon, H.R.; Chun, M.W.; Jung, Y.H.; Jeong, L.S.: J. Org. Chem. 66, 2001, 6490-6494; sowie Ovaa, H.; Codée, J.D.C.; Lastdrager, B.; Overkleeft, H.S.; van der Marcel, G.A.; van Boom, J.H.: Tetrahedron Lett. 39, 1998, 7987-7990.

Author(s): H.F. Olivo and J. Yu
Title: Enantioselective syntheses of 5´-homo-carbocyclic nucleosides
Tetrahedron: Asymmetry Vol. 8, No. 22, p. 3785-3788 (1997); ISSN: 0957-4166;

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Glyoxalsäure in Wasser; 4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one

Author(s): H.F. Olivo and J. Yu
Title: Practical enantiodivergent syntheses of both enantiomers of carbovir, 159U89 and six-membered ring analogues
J. Chem. Soc., Perkin Trans. 1, p. 391-392 (1998);

keywords: Carbanucleoside; Carbovir; 4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Glyoxalsäure in Wasser

Author(s): R.A. MacKeith, R. McCague, H.F. Olivo, C.F. Palmer and S.M. Roberts
Title: Conversion of (-)-4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one into the anti-HIV agent Carbovir
J. Chem. Soc., Perkin Trans. 1, p. 313-314 (1993);

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Glyoxalsäure in Wasser; 4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one

Author(s): V.K. Aggarwal, N. Monteiro, G.J. Tarver and S.D. Lindell
Title: Palladium-catalyzed substitution of unsaturated lactones. Application to the synthesis of Carbocyclic polyoxins and Nikkomycins
J. Org. Chem. Vol. 61, p. 1192-1193 (1996); ISSN: 0022-3263;

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Glyoxalsäure in Wasser; 4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one

Author(s): V.K. Aggarwal and N. Monteiro
Title: Asymmetric total synthesis of (+)-carbocyclic uracil polyoxin C
J. Chem. Soc., Perkin Trans. 1, p. 2531-2537 (1997);

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Glyoxalsäure in Wasser; 4-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one

Author(s): M.J. Mulvihill, M.D. Surman and M.J. Miller
Title: Regio- and stereoselective Fe(III)- and Pd(0)-mediated ring opening of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene systems
J. Org. Chem. Vol. 63, p. 4874-4875 (1998); ISSN: 0022-3263;

keywords: Aminocycopentenol-Derivate; 4-Aminocyclopenten-4-ol; Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylhydroxamsäure; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Hydroxamsäurederivaten; 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene; N,O-Hydroxamsäurespaltung mit Eisen(III)-salzen; N-Hydroxycarbonsäureamid

Author(s): P.F. Vogt, J.G. Hansel and M.J. Miller
Title: Asymmetric Synthesis of an important precursor to 5´-nor carbocyclic Nucleosides
Tetrahedron Lett. Vol. 38, No. 16, p. 2803-2804 (1997); ISSN: 0040-4039;

keywords: Aminocycopentenol-Derivate; 4-Aminocyclopenten-4-ol; Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylhydroxamsäure; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Hydroxamsäurederivaten; 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene; N,O-Hydroxamsäurespaltung mit Eisen(III)-salzen; N-Hydroxycarbonsäureamid

Author(s): M. Cowart, M.J. Bennett and J.F., jr. Kerwin
Title: Synthesis of novel carbocyclic Adenosine analogues as Inhibitors of Adenosine Kinase
J. Org. Chem. Vol. 64, p. 2240-2249 (1999); ISSN: 0022-3263;

keywords: Aristeromycin; Neplanocin A; Noraristeromycin; Aminocycopentenol-Derivate; 4-Aminocyclopenten-4-ol; Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 6-Chlorpurin; Hetero-Diels-Alder-Reaktion zwischen Cyclopentadien and Hydroxamsäurederivaten; 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene; N,O-Hydroxamsäurespaltung; N-Boc-N-Hydroxycarbaminsäure; N-Boc-N-Hydroxycarbamat

Author(s): H.T. Crimmins and B.W. King
Title: An efficient asymmetric approach to carbocyclic nucleosides: asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase
J. Org. Chem. Vol. 61, p. 4192-4193 (1996); ISSN: 0022-3263;

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylcarbonates mit 2-Amino-6-chlorpurin; Ringbildungs-Metathese; Olefin-Metathese; Grubbs-Katalysator; Evans-Auxiliar; Bildung eines cyclischen Carbonates versus eines 1,3-Dicarbonates unter verschiedenen Acylierungsbedingungen

Author(s): N.S. Sirisoma and P.M. Woster
Title: Synthesis of protected allylic amines via Palladium(0)-catalysed amination of allylic acetates
Tetrahedron Lett. Vol. 39, p. 1489-1492 (1998); ISSN: 0040-4039;

keywords: Carbanucleoside; Carbovir; Palladium-katalysierte Aminierung eines cyclischen Allylacetates mit Phthalimid; 4-Aminocyclo-2-penten-1-ol; 4-Aminocyclopent-2-en-1-ol

Author(s): N.G. Ramesh, A.J.H. Klunder and B. Zwanenburg
Title: Enantioselective synthesis of 4-Aminocyclopent-2-ene-1-one from Tricyclo[5.2.1.0^2,6]decenyl enaminones
Tetrahedron Lett. Vol. 39, p. 1429-1439 (1998); ISSN: 0040-4039;

keywords: Carbanucleoside; 4-Aminocyclo-2-pentenol; 4-Aminocyclopent-2-en-1-ol; 4-Aminocyclopent-2-en-1-on; 4-Amino-2-cyclopenten-1-on; nucleophile Addition von Methylethylamin an 4-Hydroxycyclopentenon; Aminierung von 4-Hydroxy-2-cyclopenten-1-on; 4-Hydroxycyclopent-2-en-1-on; Cyclopentadien als Doppelbindungs-Schutzgruppe

Author(s): S.J.C. Taylor, R. McCague, R. Wisdom, K. Dickson, G. Ruecroft, F. O´Brien, J. Littlechild, S.M. Roberts and C.T. Evans
Title: Development of the biocatalytic resolution of 2-Azabicyclo[2.2.1]hept-5-en-3-one as an entry to single-enantiomer carbocyclic nucleosides
Tetrahedron: Asymmetry Vol. 4, No. 6, p. 1117-1128 (1993); ISSN: 0957-4166;

keywords: Carbanucleoside; 3-Aminocyclopent-2-en-1-carbonsäure

Author(s): S. Daluge and R. Vince
Title: Synthesis of carbocyclic Aminonucleosides
J. Org. Chem. Vol. 43, No. 12, p. 2311-2320 (1978); ISSN: 0022-3263;

keywords: Carbanucleoside; 2-Azabicyclo[2.2.1]hept-5-en-3-one; Cycloaddition zwischen 1,3-Cyclopentadien and Tosylcyanid; 4-Methylbenzolsulfonsäurecyanid; 4-Methylbenzolsulfonylcyanid; Toluolsulfonsäurecyanid; Toluolsulfonylcyanid; Diels-Alder-Reaktion

Author(s): K. Tanaka, M. Kato and F. Toda
Title: Optical Resolution of 2-Azabicyclo[2.2.1]hept-5-en-3-one by Inclusion Complexation with Brucine
Heterocycles Vol. 54, p. 405- (2001); ISSN: 0385-5414;

keywords: Carbanucleoside

Author(s): G.A. Potter, C. Garcia, R. McCague, B. Adger and A. Collet
Title: Oscillating crystallization of (+) and (-) enantiomers during resolution by entrainment of 2-azabicyclo[2.2.1]hept-5-en-3-one
Angew. Chem. Int. Ed. Engl. Vol. 35, No. 15, p. 1666-1668 (1996);

keywords: Crystallization; Enantiomeric resolution; Lactams; Oscillating systems; Carbanucleoside

Author(s): S.M. Daluge, M.T. Martin, B.R. Sickles and D.A. Livingston
Title: An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)
Nucleosides Nucleotides Nucleic Acids Vol. 19, No. 1-2, p. 297-327 (2000); ISSN: 1525-7770;

keywords: Carbanucleoside; 2-azabicyclo[2.2.1]hept-5-en-3-one
Abstract:
Ziagen, (1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]- 2-cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

Inventor(s): F. Previdoli and G. Griffith
Title: Process for the production of 2-azabicyclo[2.2.1]hept-5-en-3-one
(Lonza AG) US Pat. Appl. US 5200527, (06.04.1993); Patent Class.: C07D209/52; 548/452

keywords: Carbanucleoside, Methansulfonylcyanid, 2-azabicyclo[2.2.1]hept-5-en-3-one
Abstract:
2-Azabicyclo[2.2.1]hept-5-en-3-one is produced by Diels-Alder reaction of cyclopentadiene and methanesulfonyl cyanide and then hydrolytic cleavage of the methanesulfonyl group.

Inventor(s): W. Brieden, J. Schroer, C. Bernegger-Egli, E.M. Urban, M. Petersen, J.-P. Roduit, K. Berchtold and H. Breitbach
Title: Process for the preparation of aminoalcohol derivatives and their further conversion to (1R,4S)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl -1-methanol
(Lonza AG) US Pat. Appl. US 6,448,402, (10.09.2002); Patent Class.: 544/277; 435/280; 564/1; 564/448; Intern'l Class: C07D 473/40; C07B 209/50; C07B 231/18

keywords: Carbanucleoside, 2-azabicyclo [2.2.1] hept-5-en-3-one
Abstract
The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)-- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formula. In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopente nyl-1-methanol of the formulae and then cyclized to give the end compounds.

Cited other References:
Katagiri et al., Chem. Pharm. Bull., 39(5), 1112-1122, 1991.
Campbell et al., J. Org. Chem. 1995, 60, 4602-4616.
Taylor S. J. et al., Tetrahetron: Asymmetry vol. 4, No. 6, 1993, 1117-1128.
Park K.H. & Rappoport H., J. Org. Chem. 1994, 59, 394-399.
Martinez et al. J. Org. Chem. 1996, 61, 7963-7966.
Katagiri et al., Tetrahedron Letters, 1989, 30, 1645-1658.
Malpass & Tweedle, J. Chem. Soc., Perkin Trans 1, 1977, 874-884.
H.C. Brown et al., Inorg. Chem. 20, 1981, 4456-4457.
Balkenhohl et al., 1997, J. Prakt. Chem. 339, 381-384.
K. Faber, Biotransformation in Organic Chemistry, 2.sup.nd ed., Berlin 1995, 270-305.

Author(s): R.W. Hoffmann and U. Weidmann
Title: threo/erythro-Assigment of 1,3-diol derivatives based on 13C NMR spectra
Chem. Ber. Vol. 118, p. 3980-3992 (1985);

keywords: NMR-spektroskopische Bestimmung der Konfiguration an 1,3-Diolen; 2,4-Pentandiol

Author(s): M.E. Light, P.J. Murphy, P.M. Brown and M.B. Hursthouse
Title: 4,4-Dimethyl-3,5,8,10-tetraoxatricyclo[5.2.1.02,6]decane
Acta Cryst. Vol. 58E, No. 5, p. 560-561 (2002); ISSN: 1600-5368;

keywords: Acetalisierung; Ketalisierung; D-Ribose; 2,3-O-Isopropylidene-a-D-ribofuranosyl-1-->5-anhydride; 1,5-Anhydro-2,3-O-isopropylidene-D-ribofuranose (= 1,4-Anhydro-2,3-O-isopropylidene-D-ribopyranose)
Abstract:
The title compound, C8H12O4, is formed as a by-product in the preparation of the protected sugar 2,3-O-isopropylidene-beta-D-ribose under acid-catalysed conditions (H2SO4/acetone) from D-ribose [Fleetwood & Hughes (1999). Carbohydr. Res. 317, 204-209]. The absolute configuration was assigned on the basis of the known D-ribose configuration.

Author(s): A. Fleetwood and N.A. Hughes
Title: Convenient synthesis of 2,3-O-isopropylidene-5-thio-D-ribose and 5-thio-D-ribose; synthesis of 1,4-anhydro-2,3-O-isopropylidene-a-D-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-a-D-ribopyranose
Carbohydr. Res. Vol. 317, No. 1-4, p. 204-209 (1999); ISSN: 0008-6215;

keywords: Acetalisierung; Ketalisierung; D-Ribose; 2,3-O-Isopropylidene-a-D-ribofuranosyl-1-->5-anhydride; 1,5-Anhydro-2,3-O-isopropylidene-D-ribofuranose (= 1,4-Anhydro-2,3-O-isopropylidene-D-ribopyranose)
Abstract:
Sequential mesylation-acetylation of 2,3-O-isopropylidene-D-ribofuranose gave 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-ß-D-ribofuranose that was converted into 1-O-acetyl-5-(S)-acetyl-2,3-O-isopropylidene-5-thio-b-D-ribose, deacetylation of which gave 2,3-O-isopropylidene-5-thio-D-ribose as the b-pyranose form, which was hydrolysed to 5-thio-D-ribose. 1,4-Anhydro-2,3-O-isopropylidene-a-D-ribopyranose was obtained by sodium methoxide treatment of 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-b-D-ribofuranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-a-D-ribopyranose was similarly synthesized via 1-(S)-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-5-thio-a-D-ribofuranose.

Author(s): H. Kold, I. Lundt and C. Pedersen
Title: Synthesis of L-Ribono- and L-Lyxono-g-lactone
Acta Chem. Scand. Vol. 48, No. 8, p. 675-678 (1994);


Abstract:
L-Ribonolactone has been prepared in good yield by treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-lyxono-1,4-lactone with aqueous base. It was isolated as 3,4-O-benzylidene-L-ribono-1,5-lactone. A similar treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactone gave L-lyxonolactone, isolated as the 3,5-O-benzylidene derivative. The mechanisms of the reactions, as well as those of the reaction of 5-bromo-5-deoxy-D-ribono- and -D-lyxono-1,4-lactone, with aqueous base have been studied.

Author(s): O. Varela and P.A. Zunszain
Title: First synthesis of aldopentono-1,4-thiolactones
J. Org. Chem. Vol. 58, No. 27, p. 7860-7864 (1993);


Abstract:
A convenient synthesis of enantiomerically pure aldopentono-1,4-thiolactones is described. Thus, 4-thio-D-ribono-1,4-lactone (12) has been prepared from D-gulono-1,4-lactone (1), via its 2,3-O-isopropylidene derivative 3. The 5,6-glycol system of 3 was oxidized with NaIO4. Chemoselective reduction of the resulting aldehyde function with NaBH3CN led to 2,3-O-isopropylidene-L-lyxono-1,4-lactone (7). Tosylation of 7 and subsequent treatment of the tosylate 8 with sodium methoxide afforded methyl 4,5-epoxy-2,3-O-isopropylidene-L-lyxonate (9) as a key intermediate. Treatment of 9 with thiourea gave the 4,5-thiirane derivative having the D-ribo configuration (10). Regioselective opening of the thiirane ring and simultaneous thiolactonization took place by heating 10 with KOAc-HOAc-DMF.The resulting 5-O-acetyl-2,3-O-isopropylidene-4-thio-D-ribono-1,4-lactone (11) was readily converted, by acide removal (2% HCl) of the protecting groups, into the crystalline thiolactone 12. A similar approach was employed for the synthesis of 4-thio-L-lyxono-1,4-lactone (19), starting from D-ribono-1,4-lactone (13).

Author(s): B. V. Rao and S. Lahiri
Title: Stereoselective transformations leading to pentono-1,4-lactones
J. Carbohydr. Chem. Vol. 15, No. 8, p. 975-984 (1996); ISSN: 0732-8303;


Abstract:
The readily available 2,3-O-isopropylidene-D-erythrose has been stereoselectively transformed into L-ribono and D/L-lyxonolactone derivatives via dihydroxylation, iodolactonisation and epoxidation.Also D-ribono-1,4-lactone was converted into L-lyxono-1,4-lactone. These lactones are considered as important starting materials for the synthesis of several chiral compounds. Our observations during these transformations are also presented.

Author(s): M.G. Banwell, C. De Savi, D.C.R. Hockless, S. Pallich and K.G. Watson
Title: Syntheses of the D-aldopentoses from non-carbohydrate sources
Synlett, No. S1, p. 885-888 (1999);

keywords: D-arabinose; 1,2-diol cleavage; cis-1,2-dihydro-catechol; D-lyxono-g-lactone; D-lyxose; ozonolytic cleavage; D-ribose; radical decarboxylation; D-xylose
Abstrcat:
The cis-1,2-dihydrocatechols 5-7, which are obtained in high yield and ca. 99.8 % ee by microbial oxidation of the corresponding aromatic compound, have been converted, via reaction sequences involving three distinct types of one-carbon deletion processes, into the four D-aldopentoses.

Author(s): K. Bennis, P. Calinaud, J. Gelas and M. Ghobsi
Title: A new route to some enantiomerically pure substituted morpholines from D-ribono- and D-gulono-1,4-lactones
Carbohydr. Res. Vol. 264, No. 1, p. 33-44 (1994); ISSN: 0008-6215;

keywords: Synthesis; D-Ribono-1,4-lactone; D-Gulono-1,4-lactone; Morpholine derivatives
Abstract:
D-Ribono-1,4-lactone, after acetalation, tritylation, and reduction, leads to a cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3-O-isopropylidene-5-O-trityl-D-ribitol. The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16, which was cyclized into morpholines by the action of primary amines. Acid hydrolysis, followed by acetylation, gives the (2S)-acetoxymethyl-4-isopropyltetrahydro-1,4-oxazine (21). A similar sequence has been applied to D-gulonolactone to give access to oxazines 33, 34, and 35.

Author(s): Y. Kinoshita, J.R. Ruble and G.A. Jeffrey
Title: The crystal structure of D-ribono-1,4-lactone at -150 °C
Carbohydr. Res. Vol. 92, p. 1-8 (1981); ISSN: 0008-6215;


Abstract:
The crystal structure of D-ribono-1,4-lactone, C₅H₈O₅, at -150 °C is orthorhombic, P212121, with a=10.441(2), b=11.948(3), c=4.781(1) Angstroem, V=596.43 Angstroem (MoKa1, l=0.7107 Angstroem), Z=4, Dm=1.626 gcm^-3 (20 °C)n and Dx=1.649 gcm^-3 (-150 °C). The 1,4-lactone ring has a conformation midway between E3 and 2T3, with puckering comparable to that observed in the furanose rings of nucleosides.The C-O-C=O group has bond lengths of 1.467(1), 1.354(1), and 1.203(1) Angstroem, respectively, and is slightly non-planar, with a C-O-C=O torsion angle of 172.7 °. The molecules are linked by hydrogen bonds, which form chains.The carbonyl oxygen atom is involved in a weak, bifurcated hydrogen-bond interaction.

Author(s): H.R. Pfaendler and F.K. Maier
Title: A novel synthesis of (S)-(+)-glycerol tosylate
Liebigs Ann. Chem., p. 691-694 (1989);


Abstract:
Enantiomerically pure (S)-(+)-glycerol tosylate (3) was prepared from D-(+)-ribono-1,4-lactone (4) in 43 % overall yield.

Author(s): S. Nishimura and N. Hayashi
Title: Stereoselective and Rapid Synthesis of D-Mannose
Chem. Lett., No. 10, p. 1815-1818 (1991);

keywords: tracer element; stereoselective synthesis; d mannose; d arabinose; arabinose; zinc iodide; iodide; dichloromethane
Abstract:
During the course of our studies on labeling reactions with tracer elements, a new rapid and stereoselective synthesis of D-mannose was found. Reaction of 2,3:4,5-di-O-isopropylidene-D-arabinose with trimethylsilylcyanide and zinc iodide in dichloromethane followed by reduction gave D-mannose in good yield.

Author(s): T. Nishio, Y. Miyake, K. Kubota, M. Yamai, S. Miki, T. Ito and T. Oku
Title: Synthesis of the 4-Deoxy, 6-Deoxy, and 4,6-Dideoxy Derivatives of D-Mannose
Carbohydr. Res. Vol. 280, No. 2, p. 357-363 (1996); ISSN: 0008-6215;

keywords: Deoxymannose; Selective deoxygenation; 4,6-Dideoxy-D-lyxo-hexose

Author(s): A.S. Serianni, E.L. Clark and R. Barker
Title: Carbon-13 Enriched Carbohydrates: Preparation of Erythrose, Threose, Glyceraldehyde and Glycolaldehyde with [13C]-Enrichment in Various Carbon Atoms
Carbohydr. Res. Vol. 72, p. 79-91 (1979); ISSN: 0008-6215;


Abstract:
Two-, three-, and four-carbon aldononitriles were prepared, and catalytically reduced with palladium-barium sulfate (5%) to the coresponding aldoses in high yields at pH 1.7 ± 0.1 and atmospheric pressure. Carbon-13-enriched glycolaldehyde, glyceraldehyde, erythrose, and threose were prepared with enrichment in various carbon atoms, permitting unequivocal assignment of chemical shifts for all carbons and determination of the proportions of cyclic hemiacetals and linear gem-diol forms in solution. Carbon-carbon and carbon-hydrogen coupling-constants for the furanose ring and linear hydrates of these short-chain aldoses are reported and discussed.

Author(s): M. Mandel, T. Hudlicky, L.D. Kwart and G.M. Whited
Title: From chlorobenzene to a carbohydrate in two steps. A new chemoenzymatic synthesis of 2,3-O-isopropylidene-D-erythruronolactone
Collect. Czech. Chem. Commun. Vol. 58, No. 10, p. 2517-2522 (1993); ISSN: 0010-0765;

keywords: D-Erythrurono-1,4-lactone; Erythruronolactone acetonide; 2,3-O-Isopropylidene-D-erythruronic acid-1,4-lactone; 2,3-O-Isopropylidene-D-erythruronolactone
Abstract:
Controlled oxidation of chloroepoxide V with two equivalents of sodium periodate furnished 2,3-O-isopropylidene-D-erythruronolactone (I) in 63 % yield. This procedure was augmented by combining the protection of diol III, the oxidation of acetonide IV to V, and the subsequent oxidative cleavage to I into one operation which yielded, on medium scale, the title lactone in 51% yield. detailed procedure of preparation and physical constants are provided for lactone I.
See also: Hudlicky, T.; Mandel, M.: US Pat. Appl. US 5442079 (Virginia Polytechnic Inst. State Univ.)

Inventor(s): T. Hudlicky and M. Mandel
Title: Method for preparing erythruronolactone
(Virginia Polytechnic Inst. State Univ.) US Pat. Appl. US 5442079, (15.08.1995); Patent Class.: C07D493/04

keywords: D-Erythrurono-1,4-lactone, Erythruronolactone acetonide, 2,3-O-isopropylidene-D-erythruronolactone
corresponding patents: DE69411730D, DE69411730T, EP0698026, JP8511244T, WO9426748

Abstract:
There are described improved processes for the synthesis of a desired lactone useful as a synthon, the improved processes comprising oxidizing a protected arene diol with permanganate and periodate or subjecting a substituted epoxydiol to periodate oxidation to yield the desired lactone.
(Note: The nomenclature of the compound L-erythruronolactone, as named in this Pat. Appl., is wrong. The procedure described herein gives D-erythruronolactone).
For correction and notes cf. also: Mandel, M.; Hudlicky, T.; Kwart, L.D.; Whited, G.M.: Collect. Czech. Chem. Commun. 58(10), 1993, 2517-2522.

Inventor(s): M. Mitsuaki, T. Fujio and S. Kaisuke
Title: Preparation of Ribono-1,4-lactone derivative
(Otsuka Seiyaku KK) Jpn. Kokai Tokkyo Koho JP 59141572, (14.08.1984); Patent Class.: C07D307/32

keywords: 5-O-Benzoyl-ribono-1,4-lactone, 5-O-Trityl-ribono-1,4-lactone, Trityloxy-D-Ribonolactone
Korrespondierende Patentschriften: JP59141572, P1743100C, JP4028706B
---------------------------------------
Abstract:
PURPOSE: To obtain the titled compound useful as a synthetic intermediate for oligosaccharides or nucleotides having the physiological activity in high yield and purity, only by oxidizing a 2(5H)-furanone derivative in the presence of a crown ether and/or phase transfer catalyst as a catalyst.
CONSTITUTION: A 2(5H)-furanone derivative of formula I (R is 1-10C alkyl, benzoyloxy, phenyl lower alkoxyl or phenyl lower alkylsilyloxy) e.g. 5-benzoyloxymethyl-2(5H)-furanone, is oxidized with an oxidizing agent, e.g. potassium permanganate, in the presence of a crown ether, e.g. dicyclohexano-18-crown-6- ether, and/or a phase transfer catalyst, e.g. benzyltriethylammonium chloride, in an amount of 5-20mol% based on the compound of formula I to give the aimed compound of formula II, e.g. 5-O-benzoyl-ribono-1,4-lactone.

Author(s): Z. Hricoviniova-Bilikova, M. Hricovini, M. Petrusova, A.S. Serianni and L. Petrus
Title: Stereospecific Molybdic Acid-Catalyzed Isomerization of 2-Hexuloses to Branched-Chain Aldoses
Carbohydr. Res. Vol. 319, No. 1-4, p. 38-46 (1999); ISSN: 0008-6215;

keywords: branched-chain aldoses; 2-C-(Hydroxymethyl)aldoses; Molybdic acid-catalysis; carbon-skeleton rearrangement; D-(3-13C)-fructose; mechanism study
Abstract:
On treatment with a catalytic amount of molybdic acid in aqueous solution, the 2-ketohexoses D-fructose, L-sorbose and D-tagatose undergo a stereospecific intramolecular rearrangement to give the corresponding 2-C-(hydroxymethyl)aldoses, 2-C-(hydroxymethyl)-D-ribose (D-hamamelose), 2-C-(hydroxymethyl)-D-lyxose, and 2-C-(hydroxymethyl)-D-xylose, respectively. At equilibrium, the ratio of 2-ketose to 2-C-(hydroxymethyl)aldose ranged from 14:1 (fructose) to 32:1 (sorbose). A similar treatment of D-psicose failed to yield a significant amount of the corresponding branched-chain aldose. The equilibria can be shifted with the addition of boric acid to the reaction mixture; under these conditions, ratios of 3:1 and 7:1 were obserwed for D-fructose and L-sorbose, respectively. A mechanistic study with D-(3-13C)fructose afforded D-(1-13C)hamamelose, thus confirming C-3-C-4 bond cleavage with concomitant C-2-C-3 transposition suggested from recent studies with D-(2-13C)fructose.

Author(s): M.L. Hayes, N.J. Pennings, A.S. Serianni and R. Barker
Title: Epimerization of Aldoses by Molybdate Involving a Novel Rearrangement of the Carbon Skeleton
J. Am. Chem. Soc. Vol. 104, No. 24, p. 6764-6769 (1982);


Abstract:
The molybdate-catalyzed C-2 epimerization of aldoses has been investigated by using 13C- and 2H-enriched compounds and 75-MHz 13C NMR spectroscopy.The epimerization product of D-(1-13C)mannose was exlusively D-(2-13C)glucose, demonstrating that the reaction involves a 1,2-shift of the carbon skeleton resulting in inversion of configuration at C-2.All of the aldotetroses, aldopentoses, and aldohexoses examined reacted similarly, producing equilibrium mixtures of the starting (1-13C)aldose and the 2-epimeric 2-13C product.Reaction of D-(1-13C,2H)monnose and D-(1,3-13C,3-2H)mannose in H2O and D-mannose in 2H2O demonstrated that the epimerization occurs without C-3 transposition or C-H bond breaking.Studies with aldose analogues including mannitol, 3-deoxy-D-arabino-hexose, 4-deoxy-D-lyxo-hexose, lactose, and 4,6-O-ethylidene-D-glucose suggest that the reactive molybdate complex involves the carbonyl oxygen and three hydroxylic oxygens of the aldehyde form of aldoses.The rates of reaction are influenced by the ability of the ring forms of the starting aldose to form stable unreactive molybdate complexes.Slower secondary reactions involving the simultaneous inversion of configuration of C-2 and C-3 occur without carbon skeletal rearrangement.

Author(s): S. Zhao, L. Petrus and A.S. Serianni
Title: 1-Deoxy-D-xylulose: synthesis based on molybdate-catalysed rearrangement of a branched-chain aldotetrose
Org. Lett. Vol. 3, No. 24, p. 3819-3822 (2001);

keywords: 2-C-(Hydroxymethyl)-D-erythrose; 2,3-O-isopropylidene-D-erythrono-1,4-lactone; Molybdic acid catalysis; Carbon-skeleton rearrangement

Author(s): H.S. Isbell, H.L. Frush, R. Naves and P. Soontracharoen
Title: Degradation of 2-deoxyaldoses by alkaline hydrogen peroxide
Carbohydr. Res. Vol. 90, No. 1, p. 111-122 (1981); ISSN: 0008-6215;


Abstract:
Reaction of 2-deoxy--arabino-hexose, 2-deoxy--lyxo-hexose, and 2-deoxy--erythro-pentose with alkaline hydrogen peroxide in the presence of magnesium hydroxide afforded the corresponding 2-deoxyaldonic acid, the 1,4-lactone, and the 1-O-formyl derivative of the next lower alditol. The 2-deoxyaldonic acids were separated in 60–80% yields, as new, crystalline lithium salts. The 1,4-lactones were obtained under conditions that precluded intermidiate formation of the free acids: presumably, the reaction proceeded by way of an intermediate, furanosyl hydroperoxide, which was converted into the lactone by elimination of water. With an excess of alkaline hydrogen peroxide, in the absence of magnesium hydroxide, the substrates were degraded to formic acid, with concurrent decomposition of hydrogen peroxide. It is shown that decomposition of hydrogen peroxide is catalyzed by hydroperoxide anion, and that it takes place by both a chain, and a non-chain, process. The decomposition reactions afford an abundant source of hydroxyl radical capable of oxidizing a wide variety of compounds.

Author(s): A.J. Stewart, R.M. Evans, A.C. Weymouth-Wilson, A.R. Cowley, D.J. Watkin and G.W.J. Fleet
Title: 2-Deoxy-L-ribose from an L-arabinono-1,5-lactone
Tetrahedron: Asymmetry Vol. 13, No. 24, p. 2667-2672 (2002); ISSN: 0957-4166;


Abstract:
A practical synthesis of 2-deoxy-L-ribose from L-arabinose depends on the efficient reduction by iodide of a triflate to a lactone. The X-ray crystal structure of 3,4-O-isopropylidene-L-arabinono-1,5-lactone is reported.

Author(s): L.M. Lerner
Title: An unexpected formation of 2,3-O-isopropylidene-b-L-erythrofuranosyl 2,3-O-isopropylidene-b-L-erythrofuranoside from 2,3-O-isopropylidene-L-erythrose
Carbohydr. Res. Vol. 182, No. 2, p. 287-289 (1988); ISSN: 0008-6215;

keywords: dimerization of erythrose with forming a non-reducing sugar
Abstract:
An unexpected formation of 2,3-O-isopropylidene-b-L-erythrofuranosyl 2,3-O-isopropylidene-b-L-erythrofuranoside from 2,3-O-isopropylidene-L-erythrose is observed.

Inventor(s): K. Ladenburg, R. Babson, E. Tishler and M. Tishler
Title: Tetraacetly ribonic acid and a process for its preparation
(Merck & Co., New Jersey, USA) US Pat. Appl. US 2429937, (1.10.1942)

keywords: 2,3,4,5-Tetraacetyl-D-ribonic acid, 2,3,5-Triacetyl-D-ribono-g-lactone
Abstract:
A process is claimed for the preparation of 2,3,4,5-Tetraacetyl-D-ribonic acid free from 2,3,5-Triacetyl-D-ribono-g-lactone, which is usally one impurity present in other preparation procedures. Thus, a salt of ribonic acid, especially cadmium ribonate or calcium ribonate, is treated with acetanhydride and gaseous hydrogen chloride is passed into the suspension, till absorption of hydrogen chloride ceased. After filtration of the precipitated salts, the filtrate was evaporated to dryness and the residue was recrystalised to afford the title product in 85 % yield.

Inventor(s): H. Hiroshi, T. Takashi and H. Masahika
Title: Method of producing solution containing D-ribose
(Tokyo Tanabe Co., Japan) US Pat. Appl. US 4602086, (22.07.1986); Patent Class.: C07H1/00; C07H3/02


Equivalents: DE3437571
----------------------------------
Abstract:
A D-ribose-containing solution is produced in a high epimerization ratio, such as 60-94 %, by epimerizing D-arabinose dissolved in an adequate solvent in the presence of a molybdic acid ion and a boric acid compound. The solution is useful as an inexpensive material on the industrial syntheses of vitamin B₂ or nucleic acids.

Inventor(s): H. Hiroshi, T. Takashi and H. Masahika
Title: Production of aqueous solution containing D-ribose
(Tokyo Tanabe Co., Japan) Jpn. Kokai Tokkyo Koho JP 60081196, (09.05.1985); Patent Class.: C07H3/02


Equivalents: JP1745135C, JP4032833B
---------------------------------------
Abstract:
PURPOSE: To obtain D-ribose useful as a synthetic raw material for vitamin B₂ industrially and advantageously at a low cost, by epimerizing D-arabinose in an aqueous solution in the presence of molybdenic ions as a catalyst and further a boric acid compound.

CONSTITUTION: D-Arabinose is dissolved in water in an amount of preferably 0.5-1 times of that of the D-arabinose to give an aqueous solution, and molybdenic ions, e.g. ammonium molybdate, in an amount of preferably 5-10 weight-% (expressed in terms of ions) based on the D-arabinose as a catalyst are added to the resultant aqueous solution. A boric acid compound, e.g. boric acid or sodium borate, in a molar amount of preferably 1.5-3 times of that of the D-arabinose is then added thereto, and the pH is preferably adjusted to 3-3.5. The adjusted mixture is then reacted at 95 °C for 30 min to carry out epimerization and afford the aimed aqueous solution containing the D-ribose.

Inventor(s): H. Hiroshi, T. Takashi and H. Masahika
Title: Production of Ribose
(Tokyo Tanabe Co., Japan) Jpn. Kokai Tokkyo Koho JP 61212592, (20.09.1986); Patent Class.: C07H3/02; B01J39/04; C07H1/00


Equivalents: JP1848238C, JP5058438B
--------------------------------
Abstract:

PURPOSE: To obtain the titled compound in high yield, by carrying out the epimerization of D-arabinose using a molybdic acid compound as a catalyst in the presence of a boric acid compound, and treating the reaction liquid with a column of a metal-type cation exchange material.

CONSTITUTION: D-arabinose used as the starting raw material is epimerized by heating preferably at 50-100 °C in water, organic solvent or hydrous organic solvent in the presence of a molybdic acid compound (preferably a VI-valent compound) and a boric acid compound. The obtained reaction liquid is passed through a column packed with a 2- or 3-valent metal-type cation exchange material (preferably polystyrenesulfonic acid-type strongly acidic ion exchange resin converted to Ca-type, etc.) and eluted usually with water to separate the objective compound. The amount of the boric acid compound is preferably 1.5-3 mol per 1 mol of the raw material.

Inventor(s): H. Hiroshi, T. Takashi and H. Masahika
Title: Production of solution containing D-Ribose
(Tokyo Tanabe Co., Japan) Jpn. Kokai Tokkyo Koho JP 60115595, (22.06.1985); Patent Class.: C07H3/02


Equivalents: JP1745139C, JP4032834B
---------------------------------------------
Abstract:
PURPOSE: To obtain industrially and advantageously D-ribose useful as a synthetic raw material for vitamin B₂, by the presence of a boric acid compound in a solution containing D-arabinose in epimerizing the solution in the presence of molybdic acid ions as a catalyst.

CONSTITUTION: D-Arabinose is dissolved in a solvent, e.g. ethanol, in an amount of preferably 0.5-3 times (weight/volume) of that of the D-arabinose, and molybdic acid ions, e.g. ammonium molybdate as a catalyst, and a boric acid compound, preferably boric acid, in a molar amount of preferably 1.5-3 times of that of the D-arabinose are added to the solution. The resultant mixture is then reacted preferably at 90-95 °C for 30-60 min to epimerize the D-arabinose and give the aimed solution containing D-ribose.

Inventor(s): W. Dobler and J. Paust
Title: Continuous epimerization of sugars, in particular D-arabinose to D-ribose
(BASF AG) US Pat. Appl. US 5015296, (14.05.1991); Patent Class.: C13K13/00; C07H3/02


Equivalents: DE3714473, DK228988, EP0288847, A3, B1, JP63280090
---------------------------------------------
Abstract:
Pentoses and hexoses are continuously epimerized by heating a sugar in solution in a solvent in the presence of a basic anion exchanger charged with a molybedenum(VI) compound by preparing a D- or L-sugar having cis-disposed OH groups in the 2- and 3-positions of the sugar by continuously passing a homogeneous solution of the corresponding sugar having transdisposed OH groups in the 2- and 3-positions of the sugar in a mixture of water and methanol or ethanol at from 70 ° to 100 °C, preferably at from 73 ° and 80 °C, through a reaction tube which contains the basic anion exchanger charged with the molybdenum(VI) compound, this method being suitable in particular for epimerizing D-arabinose to prepare D-ribose required for the production of riboflavin.

Author(s): M.-Y. Chen, J.-L. Hsu, J.-J. Shieb and J.-M. Fang
Title: Direct Oxidative Amidation of Aldoses by Iodine in Ammonia Water
J. Chin. Chem. Soc. Vol. 50, No. 1, p. 129-133 (2003);

keywords: Aldoses; Amides; Iodine; Ammonia; acdonic acids; aldonic acid amides; D-Ribonamide, D-Arabinamide, Xylonamide
Abstract:
Aldopentoses, aldohexoses and the benzylated derivatives reacted with iodine in ammonia water at room temperature to give their corresponding saccharide amides in high yields. The reactions proceeded with oxidation of the aldose hemiacetals by iodine to generate the saccharide lactone intermediates, which underwent ammonolysis in situ to give the saccharide amides.

Author(s): X.-Q. Yin, V.P. Rajappan, A. Roy and S.W. Schneller
Title: A Facile Synthesis of (-)-(4R,5R)-4,5-(Isopropylidenedioxy)-2-cyclopentenone, a Useful Precursor to d-Like Carbanucleosides
Synth. Commun. Vol. 33, p. 1477-1481 (2003); ISSN: 0039-7911;


Abstract:
A facile synthesis of (-)-(4R,5R)-4,5-(isopropylidenedioxy)-2-cyclopentenone ((-)-2), as a precursor to d-like carbanucleosides, is described in 5 steps from (1S,4R)-4-acetoxycyclopent-2-en-1-ol (3). Compound 3 has also been described in the literature as amenable to the formation of (+)-2, thus making both the d-like and l-like carbanucleosides available from the same readily available 3.

Title: Zinc aldonates
(Poor & Co.) Brit. Pat. Appl. GB 693592 , (01.07.1053); Patent Class.: C07C59/105

keywords: preparation of zinc aldonates from aldonic acids, Zinc ribonate, Zinc arabonate
Abstract:
New zinc salts of aldonic acids are obtained by reacting together one mole of zinc oxide and two moles of an aqueous solution of an aldonic acid at elevated temperature. The aldonic acids used are derived from aldose sugars by oxidation. Suitable acids are, for example, gluconic, mannonic, galactonic and arabonic acids. In the example, zinc gluconate is prepared by heating a gluconic acid solution with zinc oxide.

Inventor(s): Z.V. Pushkareva, A. Grishakov, V.I. Nifontov, G.A. Vavilov, V.S. Mokrushin, N.A. Belayev and E.M. Emelina
Title: Method for isolating chemically pure D-ribose from its aqueous solution containing admixtures of D-arabinose, D-ribono-g-lactone, ribit and sodium chloride
(Uralsky Politekhn Inst.) USSR Pat. Appl. SU 1116038, (30.09.1984)

Author(s): M.E. Jung and Y. Xu
Title: Efficient synthesis of L-ribose and 2-deoxy L-ribose from D-ribose and L-arabinose
Tetrahedron Lett. Vol. 38, No. 24, p. 4199-4202 (1997);


Abstract:
Interconversion of the ends of D-ribose (2) afforded in 6 steps and 45 % overall yield L-ribose (1), from which 2-deoxy L-ribose (12) was easily prepared. In addition, the inexpensive L-arabinose (13) was also converted into 2-deoxy L-ribose (12) via a reductive radical rearrangement of the arabinopyranosyl bromide (14).

Author(s): P. Kanda and M.A. Wells
Title: A simplified procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol from L-arabinose
J. Lipid Res. Vol. 21, No. 2, p. 257-258 (1980);


Abstract:
A new procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol is described. L-arabinose is converted to its 4,5-monoisopropylidene diethyl mercaptal derivative. This compound is then subjected to periodate oxidation and borohydride reduction. Following neutralization, the aceton-glycerol is extracted from the aqueous solution into chloroform. Evaporation of the chloroform and subsequent distillation yielded pure 2,3-O-isopropylidene-sn-glycerol ([a]D22 = -14.5 ° (in substance)) in an overall yield of 15-25 %.

Author(s): H. Kazuhara, H. Terayama, H. Ohrui and S. Emoto
Title: Preparation of L-lyxose and some of its furanose derivatives
Carbohydr. Res. Vol. 20, No. 1, p. 165-169 (1971);

Author(s): D.R. Kodali
Title: Improved method for the synthesis of 1- or 3-acyl-sn-glycerols
J. Lipid Res. Vol. 28, No. 4, p. 464-469 (1987);


Abstract:
Optically active 1- or 3-acyl-sn-glycerols were synthesized from 2,3- or 1,2-isopropylidene-sn-glycerols, respectively. The 2,3- or 1,2-isopropylidene-sn-glycerols were condensed with appropriate long saturated or unsaturated fatty acids and the resulting acyl isopropylidene compounds were treated with dimethylboronbromide at - 50 °C to give the title compounds. The ketal cleavage of acyl isopropylidene-sn-glycerols by dimethylboronbromide to produce the long 1- or 3-acyl-sn-glycerols was effective and gave good yields (70-90%). The reaction conditions were mild and there was no acyl migration, as shown by optical rotation of the monoacyl-sn-glycerols. The synthesis of 2,3-isopropylidene-sn-glycerol was improved to give an overall yield of 40 % from L-arabinose. L-Arabinose was first converted to its 1,1'-diethylmercapto derivative and then condensed with 2-methoxypropene to yield 1,1'-diethyl-mercapto-4,5-isopropylidene-L-arabinose. Oxidation of this compound with sodium periodate followed by reduction with sodium borohydride under alkaline conditions yielded 2,3-isopropylidene-sn-glycerol [a]22D = -14.90 °, neat (Lit. 8 [a]22D = -14.5 °, neat; 14 [a]25D = -10.8 °; methanol c = 16.9). The optical purity of isopropylidene-sn-glycerols was determined as benzoyl derivatives on a high performance liquid chromatographic column packed with a chiral stationary phase.

Author(s): N.A. Hughes and P.R.H. Speakman
Title: New isopropylidene derivatives of D-ribose: 1,2:3,4-di-O-isopropylidene-D-ribofuranose and 1,2-O-isopropylidene-D-ribopyranose
Carbohydr. Res. Vol. 1, No. 2, p. 171-175 (1965); ISSN: 0008-6215;


Abstract:
Acetonation of D-ribose gave, among the already described 2,3-O-isoprpylidene-D-ribofuranose as the main product, 1,2:3,4-di-O-isopropylidene-D-ribofuranose and 1,2-O-isopropylidene-D-ribopyranose as minor by-products. Further, 1,5-anhydro-2,3-O-isopropylidene-D-ribofuranose and dimeric 1,5´:1´,5-dianhydro-di(2,3-O-isopropylidene-D-ribofuranose) were isolated in poor yields.
Compare also: Hughes, N.A.; Speakman, P.R.H.: Benzoate displacements on sulphonate esters of some 1,2-O-isopropylidenepentofuranoses, Carbohydr. Res. 1(5), 1966, 341-348.

Author(s): W. Funcke, A. Klemer and E. Meissner
Title: Über den oxidativen Kettenbruch von Amadoriverbindungen zu Foramidinium-D-arabinonaten
Carbohydr. Res. Vol. 79, p. 298-302 (1980); ISSN: 0008-6215;

keywords: D-arabinonic acid-1,4-lactone

Author(s): R.J. Abraham, L.D. Hall, L. Hough, K.A. McLauchlan and H.J. Miller
Title: A proton resonance study of conformations of Carbohydrates in solution. Part III. D-Ribono-1,4-lactone and its 2,3-O-Isopropylidene derivative.
J. Chem. Soc., p. 748-749 (1963);

Author(s): R. Sharma and V.E. Marquez
Title: Rapid synthesis of 5-O-(tert-butyldiphenylsilyl)-2-deoxy-L-ribonolactone
Synth. Commun. Vol. 24, No. 13, p. 1937-1945 (1994); ISSN: 0039-7911;


Abstract:
A convenient, four-step synthesis of the title compound (1) in 21 % overall yield from arabinose is described. Selective formation of the 2-O-phenoxythiocarbonyl derivate 6 and its tributyltin hydride / azobis(isobutyronitrile) deoxygenation performed in the presence of an unprotected hydroxyl group are highlighted.

Author(s): B. Kaskar, G.L. Heise, R.S. Michalak and B.R. Vishnuvajjala
Title: A convenient large scale synthesis of protected D-Ribonolactone from D-Ribose
Synthesis, p. 1031-1032 (1990); ISSN: 0039-7881;


Abstract:
A simple and efficient synthesis of protected D-ribonolactone, a key chiral precursor used in the syntheses of neplanocin A and cyclopentenylcytosine from readily available D-ribose is reported. D-Ribose is converted to its 2,3-O-isopropylidene derivate, and the C-5-OH-position is protected with tert.-butyldimethylsilyl protecting group. 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribose is oxidized to 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-ribono-1,4-lactone.

Author(s): G. Hu, M. Zimmermann, C.V. Ramana and A. Vasella
Title: Cyclopentanes from N-amino-glyconolactams. A synthesis of mannostatin A
J. Chem. Soc., Chem. Commun., No. 8, p. 952-953 (2003);


Abstract:
Oxidation of a N-amino-ribonolactam with lead tetraacetate yields two cyclopentanes; the major one was transformed into the -mannosidase inhibitor mannostatin A.

Author(s): S. Takano, K. Inomata and K. Ogasawara
Title: Conversion of 2,3-O-cyclohexylidene-(D)-ribonolactone into 2,3-O-cyclohexylidene-(L)-ribonolactone
Heterocycles Vol. 27, No. 10, p. 2413-2415 (1988); ISSN: 0385-5414;


Abstract:
A convenient method for chirality inversion of 2,3-O-cyclohexylidene-D-ribonolactone to 2,3-O-cyclohexylidene-L-ribonolactone has been established.

Author(s): G.Y. Song, V. Paul, H. Choo, J. Morrey, R.W. Sidwell, R.F. Schinazi and C.K. Chu
Title: Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus
J. Med. Chem. Vol. 44, No. 23, p. 3985-3993 (2001);


Abstract:
Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC₅₀ 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC₅₀ 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC₅₀ 58.9 muM).

Author(s): Z. Stejskal
Title: Das Kaliumsalz der D-Arabonsäure im Gemisch mit Invertzucker
Analytical and Bioanalytical Chemistry Vol. 237, No. 4, p. 309 (1968); ISSN: 1618-2642;

keywords: D-arabionic acid; D-arabonic acid potassium salt
DOI: 10.1007/BF00499378
Bericht über die Fortschritte der analytischen Chemie, III. Analyse organischer Stoffe

Author(s): N.A. Hughes and P.R.H. Speakman
Title: Benzoate displacements on sulphonate esters of some 1,2-O-isopropylidenepentofuranoses
Carbohydr. Res. Vol. 1, No. 5, p. 1-348 (1965); ISSN: 0008-6215;


Abstract:
The benzoate displacement of sulphonate derivatives of several 1,2-O-isopropylidene-pentofuranoses has been studied. Displacement occurs readily with 5-sulphonates, more slowly with endo-3-sulphonates, and not at all with exo-3-sulphonates. Neighbouring-group participation from 5-benzoate groups does not assist in the displacement of the 3-sulphonates.
Compare also: Hughes, N.A.; Speakman, P.R.H.: New isopropylidene derivatives of D-ribose, Carbohydr. Res. 1(2), 1966, 171-175.

Author(s): V.G. Mairanovskii, Yu. Sviderski and A.M. Ponomarev
Title: Polarographic investigation of D-ribono-g-lactone
Chem.-Pharm. J. Vol. 13, No. 3, p. 283-285 (1979); ISSN: 0091-150X;
Khim.-Farm. Zh. Vol. 13, No. 3, p. 62-65 (1979); ISSN: 0023-1134;

Author(s): V.M. Svetlaeva, L.M. Kirshchenya and M.Ts. Yanotovskii
Title: Analysis by gas-liquid chromatography of ribose and intermediates in its synthesis
Chem.-Pharm. J. Vol. 11, No. 2, p. 275-277 (1977); ISSN: 0091-150X;
Khim.-Farm. Zh. Vol. 11, No. 2, p. 132-134 (1977); ISSN: 0023-1134;

Author(s): A.K. Kaz'mina and N.S. Fadeeva
Title: Potentiometric determination of calcium in monitoring d-ribose production
Chem.-Pharm. J. Vol. 15, No. 2, p. 149-150 (1981); ISSN: 0091-150X;
Khim.-Farm. Zh. Vol. 15, No. 2, p. 115-117 (1981); ISSN: 0023-1134;

Author(s): Hitesh Batra, Robert M. Moriarty, Raju Penmasta, Vijay Sharma, Gabriela Stanciuc, James P. Staszewski, Sudersan M. Tuladhar, David A. Walsh, Satyanarayana Datla and Sunderraj Krishnaswamy
Title: A concise, efficient and production-scale synthesis of a protected L-lyxonolactone derivative: an important aldonolactone core
Org. Process Res. Dev. Vol. 10, No. 3, p. 484-486 (2006); ISSN: 1083-6160;

keywords: 2,3-O-isopropylidene-L-lyxonolactone; 2,3-O-Isopropylidene-D-ribonolactone
Abstract:
A multikilogram-scale synthesis of L-lyxonolactone-2,3-O-isopropylidene is reported. It proceeds efficiently from an optimized, large-scale, aqueous bromine oxidation of D-ribose to D-ribonolactone including a one-pot isopropylidene formation, and subsequent conversion of the D-ribonolactone-2,3-O-isopropylidene to L-lyxonolactone-2,3-O-isopropylidene via the derived C₅-mesylate and intramolecular relactonization of the product of aqueous potassium hydroxide cleavage of the D-ribonolactone ring. The inversion of configuration at the C₄-chiral center is understood in terms of an intermediating C₄-C₅-epoxide. The overall process is noteworthy for its operational simplicity, stereochemical integrity, and use of inexpensive chemicals.