Rhenium(V)-catalyzed synthesis of 1,1'-2-deoxy thioglycosides.

As stable glycomimetics, thioglycosides are important tools for the investigation of biological processes and discovery of new drugs. In this note, we report a ReOCl3(SMe2)(OPPh3) catalyzed coupling reaction between β-glycosyl thiols (1-thio sugars) and glycals for the preparation of 1,1'-α,β-2-deoxy thioglycosides, which are glycomimetics of natural trehalose and 2-deoxy glycosides. Furthermore, an S-linked trisaccharide was successfully obtained by successive employment of the Re(V) catalyzed thioglycosylation protocol.