trans-Stilbene C-Glycosides: Synthesis by a Microwave-Assisted Heck Reaction and Evaluation of the SGLT-2 Inhibitory Activity

Abstract

A protocol for the microwave-assisted Heck coupling reaction of C-aryl glycosides and styrenes has been developed for the synthesis of mono-and bis(C-glycoside) stilbenes. This method exclusively provides C-glycoside trans-stilbenes in good yields. The Pd-catalyzed Heck coupling re-action was successfully applied to various functionalized C-glycosyl aryl iodides and various substituted styrenes to deliver several C-glycoside trans-stilbenes with high selectivity. The obtained C-glycosyl trans-stilbenes were also examined for human SGLT-2 inhibitory activity.