4′,6′-O-Benzylidene- and 4′,6′-O-p-Methoxybenzylidene-α,β-cellobiose and Their Hexa-O-β-benzoyl Derivatives

Abstract

The preparation of 4′,6′-O-benzylidenecellobiose has been improved and its p-methoxybenzylidene counterpart was prepared in a similar way. As with other alkylidene derivatives of sugars, the corresponding per-O-benzoates are versatile intermediates in carbohydrate synthesis, allowing, after hydrolytic cleavage or opening of the phenylidene ring, regioselective manipulation of hydroxyl groups in cellobiose, or access to various derivatives of lactose.

Key words

synthetic methods - carbohydrate chemistry - protecting groups - regioselectivity

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