Copper (II)-Mediated Deoxychlorinated Synthesis of Glycosyl Chlorides from Glycosyl Hemiacetals

Abstract

Herein, we report a highly efficient and mild methodology for the deoxychlorinated synthesis of glycosyl chlorides directly from readily available glycosyl hemiacetals, by using diphenylchlorophosphate in combination with copper (II) chloride. This strategy used bench-stable substrates with remarkable functional group tolerance, effectively allowing both disarmed and armed sugars in 70-90% yield. The synthesized chloroglycosides directly demonstrated broad utility in O- and N-glycosylation with saccharin, amino acid, and flavonoid, offering a general route for easy access to diverse glycoconjugates.