Synthesis of C,N-Glycosides via Brønsted Acid-Catalyzed Azidation of exo-Glycals

Abstract

The reaction of exo-glycals with azidotrimethylsilane in the presence of a Brønsted acid leads to the generation of the corresponding C,N-glycosyl azides. The majority of these glycosylation reactions proceed at room temperature with short reaction times. In addition, the targeted products were obtained in high yields with exclusive diastereoselectivity to the α-anomer in pyranose-based derivatives. Carbohydrate units based on mannose, galactose, arabinose, and ribose were also shown to proceed in high yields.