Investigations into the Chemistry of Some 1,6-Epithio and 1,6-Episeleno ß-D-Glucopyranoses

Abstract

Derivatives of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose have been shown to undergo oxidation reactions to afford the corresponding sulfoxides and sulfones. The sulfoxides participate in Pummerer reactions to afford the corresponding α-acetoxy sulfides which were then oxidized further. None of the sulfoxides, sulfones or α-acetoxy sulfides prepared were particularly efficient glycosyl donors. Also presented are crystal structures of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose S,S-dioxide and 1,6-dideoxy-1,6-episeleno-β-D-glucopyranose, interesting analogues of 1,6-anhydro-β-D-glucopyranose.