Title | Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester |
Publication Type | Journal Article |
Year of Publication | 2018 |
Authors | Manhas, S, Taylor, MS |
Journal | Carbohydrate Research |
Volume | 470 |
Pagination | 42 - 49 |
Date Published | 2018/12/01/ |
ISBN Number | 0008-6215 |
Keywords | 2-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. |
URL | http://www.sciencedirect.com/science/article/pii/S0008621518304579 |
Short Title | Carbohydrate Research |