Palladium-Catalyzed C–S Bond Formation as a Tool for Latent–Active Glycosylation

Abstract

A high-yielding palladium-catalyzed C–S cross-coupling is presented for utilization in carbohydrate chemistry as a key transformation for attachment of a second chelating sulfur atom that allows the exploitation of a latent–active glycosylation strategy with Cu(OTf) 2 as the promoter. The novel approach employs o -Br-benzyl thioglycosides as latent glycosyl donors and o -SMe-benzyl thioglycosides as the active counterparts.