A straightforward and general strategy towards 1,5-dithio-1-enopyranosides

Article abstract of DOI:10.1002/ejoc.200800314

The 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, 2008.