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Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester

TitleDehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester
Publication TypeJournal Article
Year of Publication2018
AuthorsManhas, S, Taylor, MS
JournalCarbohydrate Research
Volume470
Pagination42 - 49
Date Published2018/12/01/
ISBN Number0008-6215
Keywords2-Deoxyglycoside, Boronic acid, Catalysis, Glycosidation
Abstract

An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C–O bond formation from carbohydrate-derived hemiacetals.

URLhttp://www.sciencedirect.com/science/article/pii/S0008621518304579
Short TitleCarbohydrate Research