Synthesis of C -glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri- O -acetyl- D -glucal

We have developed an efficient, CuI-catalyzed, microwave-assisted method for the synthesis of bis-1,2,3-triazole derivatives starting from a 3,4,6-tri- O -acetyl- d -glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri- O -acetyl- d -glucal through C -glycosidation, deprotection of acetate groups to alcohols, and selective mesylation of the primary alcohol. This mesylate moiety was then converted to an azide through a microwave-assisted method with good yield. The azide, once synthesized, was then treated with different terminal alkynes in the presence of CuI to synthesize various bis-triazoles in high yields and short reaction times.