An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors.

Abstract A novel approach to the synthesis of β-glycosides of N -acetyl- d -glucosaminuronic acid, in six steps and good overall yield from N -acetyl- d -glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O -glycosidation of methyl 1,3,4-tri- O -pivaloyl- N -acetyl- d -glucosaminuronate ( 11 ). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22 , which showed inhibition of Vibrio cholerae sialidase.