Zinc Tetrafluoroborate Catalyzed Stereo- and Regioselective O-Glycosylation for the Direct Synthesis of ß-Glycosides from Armed O-Glycosyl Trichloroacetimidates.

ABSTRACT

Efficient stereo- and regioselective O-glycosylation methods remain essential to capacitate the studies of sugars and sugar derivatives in various disciplines. In this work, we demonstrated an operationally simple and cost-effective strategy for the synthesis of 1,2-trans glycosides by the activation of armed O-glycosyl trichloroacetimidates donor using zinc tetrafluoroborate. This mild, transition metal-free, and scalable approach allowed stereo- and regioselective synthesis of ß-glycosides with a wide range of acceptors containing various protecting groups/functionalities. This method is exemplified by synthesizing a branched trisaccharide fragment related to the cell wall O-polysaccharide of E. Coli O27.