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Selective acylation of methyl α-d-glucopyranoside at O-6 by reaction with hexachloroacetone and pentachloroacetone

✍ Scribed by Alan H. Haines; E.John Sutcliffe

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 359 KB
Volume: 138
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85232-0

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✦ Synopsis

The selective protection of carbohydrates and their derivatives is a subject of continuing interest1+2 and it has recently assumed increased importance as a result of the current widespread use of carbohydrates as a source of chiral building blocks for the synthesis of natural products -3 5. Therefore, the report6 that trichloroacetylation of alcohols by hexachloroacetone, in the presence of strong hydrogen-bond acceptors, is a stereoselective process, which allows, for example, the acylation of l-propanol in the presence of 2-propanol with 94% selectivity, led us to examine the applicability of this type of reaction in carbohydrate chemistry. We now report on the reaction of methyl cY-D-glucopyranoside (1) with hexachloroacetone and pentachloroacetone.

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