Regioselective Oxidative Cleavage of Benzylidene Acetals of Glycopyranosides with Periodic Acid Catalyzed by Tetrabutylammonium Bromide

Dedicated to the memory of Professor André Lubineau

Abstract

A combination of periodic acid, tetrabutylammonium bromide, and wet alumina in dichloromethane efficiently oxidized benzylidene acetals of carbohydrates to the corresponding hydroxybenzoates in excellent yields (>90%). Under these conditions, other protecting groups, such as tert-butyl(dimethyl)silyl, tert-butyl(diphenyl)silyl, and functional groups, such as epoxide, were unaffected. By varying the nature of the protecting group at the C3 position, good to high regioselectivity toward 4- or 6-benzoates was obtained.

Key words

acetals - carbohydrates - oxidation - cleavage - regio­selectivity - protecting groups

• References and Notes

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