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Synthesis of 5-thio-d-altrose and some of its derivatives

✍ Scribed by Najim A.L. Al-Masoudi; Neil A. Hughes

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
865 KB
Volume
148
Category
Article
ISSN
0008-6215

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✦ Synopsis

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 2,3anhydro-4,6-0-isopropylidene-5-thio-a-and -/3-D-allopyranosides. Epoxide opening with aqueous sodium hydroxide then gave mixtures of methyl 4,6-O-iso-propylideneJ-thio-a-or -/I-D-ahropyranosides (9) and the corresponding gluco compounds 10. Mild, acid hydrolysis converted 9 into the methyl 5-thio-a-and -/3-D-ahropyranosides and more vigorous hydrolysis gave 5-thio-D-altrose. Methyl 3,4-0-isopropylidene-5-thio-a-D-altropyranoside was obtained when the 4,6-acetal 9s was left in acidified acetone. The methyl 2,3:4,6-di-0-isopropylidene-5-thio-CYand -&D-glucopyranosides were quickly produced by the action of acidified 2,2-dimethoxypropane on the 4,6-acetals 10. Methyl 2,3,4,6-tetra-O-acetyl-a-D-altropyranoside (17a) was shown to exist mainly in the 4C, conformation, but the p anomer 17b and 1,2,3,4,6-penta-O-acetyl-5thio-B-D-altropyranose both adopt mainly the iC, conformation. *5-Thio-pyranoses, Part 10. For Part 9, see ref. 1.

πŸ“œ SIMILAR VOLUMES

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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