Palladium-Catalyzed O- and N-Glycosylation with Glycosyl Chlorides

Despite the significant progress in carbohydrate chemistry, there remains a pressing need for efficient and practical glycosylationmethods using simple glycosyl donors and with high atom economy. Herein, a new protocol for glycosylation with glycosyl chloride donors under palladium-catalyzed conditions is developed. PdII complex serves as a Lewis acid to promote the activation of glycosyl chloride for the formation of oxocarbeniumion intermediate. This new method is operationally simple, robust, and enables efficient synthesis of both O- and N-glycosides with a broad substrate scope. In particular, it offers an easy access to a range of N-ribonucleoside analogs.

Automated summary

A new protocol for glycosylation using glycosyl chloride donors under palladium-catalyzed conditions has been developed. This method is operationally simple, robust, and enables efficient synthesis of various glycosides, including N-ribonucleoside analogs.