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Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates^†

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Yoshihiro Ueda, Wataru Muramatsu, Kenji Mishiro, Takumi Furuta and Takeo Kawabata

Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

J. Org. Chem., 2009, 74 (22), pp 8802–8805

DOI: 10.1021/jo901569v

Publication Date (Web): October 15, 2009

kawabata@scl.kyoto-u.ac.jp

Abstract

Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl β-d-glucopyranoside with acid anhydrides derived from α-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67−94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78−94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R′ = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.

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History

Published In Issue November 20, 2009
Article ASAPOctober 15, 2009
Received: July 28, 2009

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Note

Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates^†