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Synthesis of 5-thio-d-arabinose and 5-thio-d-lyxose and their methyl glycopyranosides

✍ Scribed by Neil A. Hughes; Namboole M. Munkombwe


Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
871 KB
Volume
136
Category
Article
ISSN
0008-6215

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πŸ“œ SIMILAR VOLUMES


A facile synthesis of 5-thio-l-fucose an
✍ Masayuki Izumi; Osamu Tsuruta; Hironobu Hashimoto πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 English βš– 955 KB

5-Thio-L-fucopyranose tetraacetate was synthesized in 11 steps from 5-O-trityl-D-arabinofuranose or D-arabinose diethyl dithioacetal by one-carbon elongation at C-5. Highly diastereoselective addition of MeLi in ether to a 1,2-O-isopropylidene-[J-D-arabino-pentodialdo-l,4-furanose derivative was ach

Synthesis of 5-thio-d-allose and the met
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ABSTRAm 5,6-Anhydro-1,2-0-isopropylidene-3-O-methanesulphonyl-a-~-idofuranose was converted, via the related gZucod$-episulphide, into 6-0-acetyl-5-S-acetyl-1,2-O-isopropylidene-3-O-methanesulphonyl-5-thio-at-D-glucofuranose (9). Replacement of the acetyl groups of 9, or the related 3-toluene-p-sulp

Chemoenzymatic Synthesis of 5-Thio-D-xyl
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New syntheses of methyl 5-thio-Ξ²-d-arabi
✍ Neil A. Hughes; Ksenija-Maria Kuhajda; Dusan A. Miljkovic πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 English βš– 436 KB

Previously one of us reported 121 that methyl 3,4-0-isopropylidene-2-Omethanesulfonyl-5.thio-~-D-~~pyranoside (1) readily unde~ent ring ~ntra~tion in methanol to give 2,5-dideo~-2,5-epithio-o-arabinose dimethyl acetal (2). It was of interest to examine this reaction with the corresponding D-arabinos

Synthesis of 5-thio-d-altrose and some o
✍ Najim A.L. Al-Masoudi; Neil A. Hughes πŸ“‚ Article πŸ“… 1986 πŸ› Elsevier Science 🌐 English βš– 865 KB

Acid-catalysed methanolysis of 6-0-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-3-0-toluene-p-sulphonyl-a-D-glucofuranose gave the methyl 5-thio-3-0toluene-p-sulphonyl-a-and -/3-D-glucopyranosides (5). Treatment of 5 with acidified 2,2-dimethoxypropane and then sodium methoxide gave the methyl 2,3a

Synthesis and conformation of 5-thio-d-g
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Molecules whose geometry resembles that of the transition state in enzymecatalyzed reactions are known to be excellent enzyme-inhibitors. Carbohydrate substrates of glycosidases are known to produce a carboxonium 1011 111 the transition state, the geometry of which probably resembles that of a tlatt