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A SHORT SYNTHESIS OF BETA-XYLOBIOSIDES

TitleA SHORT SYNTHESIS OF BETA-XYLOBIOSIDES
Publication TypeJournal Article
Year of Publication1994
AuthorsZISER, L, Withers, SG
JournalCARBOHYDRATE RESEARCH
Volume265
Pagination9-17
Date PublishedDEC 2
ISSN0008-6215
Abstract

Benzyl 2,3,2',3',4'-penta-O-acetyl-beta-xylobioside, 2-nitrophenyl beta-xylobioside, 4-nitrophenyl beta-xylobioside, and 2-iodobenzyl 1-thio-beta-xylobioside were synthesized via a short and highly selective route. beta-D-Xylopyranosides were selectively 4-O-triethylsilylated using dibutyltin oxide and triethyhilyl chloride and subsequently 2,3-di-O-acetylated. Desilylation under acidic conditions gave the 4-unprotected xylosides which then were beta-D-xylosylated using 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl trichloroacetimidate.

DOI10.1016/0008-6215(94)00214-2