A One-Pot Synthesis of Glycosyl Amides from Glycosyl Azides Using a Modified Staudinger Reaction

Abstract

In a continuation of our research devoted to the synthesis and supramolecular assemblies of amphiphilic carbohydrates,^1–3 we report a new preparation of glycosyl amides β-3a. Interest in such compounds lies in their ability to escape glycosidases in vivo and in their use as potent nonionic biosurfactants. Several methods have already been reported in the literature for the preparation of such derivatives (Scheme 1).

Notes

The glycosyl phosphinimine intermediate β-5 can anomerize to α-5 via an open-chain zwitterionic structure.

The formation of the C-phosphonium salts 6 cannot be excluded from our experiments. Nevertheless this side-reaction, if any, seems to constitute a very minor pathway.