Catalytic stereoselective synthesis of 2-deoxy α-glycosides using glycosyl ortho-[1-(p-MeOPhenyl)Vinyl]Benzoate (PMPVB) donors

Abstract

2-Deoxy glycosyl ortho-[1-(p-MeOPhenyl)Vinyl]Benzoates (PMPVB) have been presented as stable, reactive glycosyl donors for the synthesis of 2-deoxy α-glycosides. The donors react under Brønsted acid conditions to provide the 2-deoxy-α-glycosides with very high stereocontrol. The observed high stereoselectivities were discussed with respect to the relative free energy differences between the anomeric reactive intermediates.