Organobase-catalyzed efficient synthesis of 4-acyl-5-aryl tri-substituted triazole linked N-glycosides as glycohybrids

Abstract

Herein, we report a highly efficient organobase-catalyzed method for the synthesis of fully decorated chiral 4-acyl-5-aryl-trisubstituted-1,2,3-triazole-linked N-glycosidic molecular scaffolds as glycohybrids. This process involves a base-catalyzed 1,3 dipolar cycloaddition reaction, where β-ketoesters react with various glycosyl azides in dimethyl sulfoxide at room temperature, furnishing new glycohybrids in good to excellent yields. This intermolecular reaction is metal-free, exceptionally efficient, versatile, and high-yielding, with a broad substrate scope and remarkable regioselectivity.