Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors

Abstract

Disaccharide nucleosides constitute an important group of naturally-occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O-glycosylation of nucleoside acceptors, such as adenosine, guanosine, thymidine, and cytidine, with glycosyl donors. Among the glycosyl donors tested, thioglycosides were found to give the corresponding disaccharide nucleosides in moderate to high chemical yields with the above nucleoside acceptors using p-toluenesulfenyl chloride (TolSCl) and silver triflate (AgOTf) as promoters. The interaction of these promoters with nucleoside acceptors was examined by (1)H NMR spectroscopic experiments.

Keywords: O-glycosylation; chemical glycosylation; disaccharide nucleosides; nucleosides; thioglycoside.