Stereospecific synthesis of branched-chain sugars by a novel aldol-type cyclocondensation

✍ Scribed by María-Jesús Pérez-Pérez; María-José Camarasa; Angel Díaz-Ortiz; Ana San Félix; Federico G. de las Heras

• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 995 KB
• Volume: 216
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)84176-s

✦ Synopsis

A procedure for the preparation of branched-chain sugars having highly functionalised C-branches is reported. Reaction of furanos-3-uloses, pyranos-3-uloses, or pyranos-2-uloses with sodium cyanide followed by mesylation of the corresponding cyanohydrin afforded cc-mesyloxynitriles which, on treatment with base, underwent aldol-type cyclocondensation to yield furanose-3-Spiro-. pyranose-3-Spiro-, and pyranose-2-spiro-5'-(4'-amino-Ir,2'-oxathiole-2',2'-dioxide) derivatives. Treatment of the furanose-3-Spiro derivatives with methanolic sodium methoxide gave C-[(E)-I-amino-2-(methoxysulfonyl)vinyl] branchedchain sugars having the same configuration as the starting cyanohydrins. * Dedicated to Professor Grant Buchanan on the occasion of his 65th birthday.