An efficient synthesis of triazolo-carbohydrate mimetics and their conformational analysis

Abstract

A chemical library of 1,2,3-triazole fused carbohydrate mimetics was constructed. To synthesize enantiomerically pure mimetics, we developed a stereo- or diastereodivergent synthetic route from D-glucose, D-mannose and D-galactose as chiral sources. In this synthesis, an In(OTf)₃-catalyzed tandem azidation–1,3-dipolar cycloaddition reaction of 1,1-dimethoxyhex-5-yne derivatives with TMSN₃ was used as the key step to construct the 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine framework. Additionally, NMR was used to carry out a conformational analysis of the synthesized mimetics, which are of structural interest since they have an N,O-acetal moiety in place of the anomeric position of normal pyranosides.