Abstract
AbstractThe synthesis of a new class of thiosugar derivatives, 1,5‐dithio‐1‐enopyranosides, has been achieved in a two‐step sequence from easily available aldofuranoses. In the first step, a carbohydrate‐derived ketene dithioacetal was formed by Peterson olefination of an aldofuranose and a lithiated α‐silyl thioacetal. In the second step, intramolecular nucleophilic substitution of an activated hydroxy group by a sulfur atom of the ketene dithioacetal function led to the target compounds in good yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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