"Boomerang" Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of C -Glycosylated Benzothiazoles from ortho -Isocyanophenyl Thioglycosides.

This paper reveals a novel "boomerang" strategy in the expedient and diastereoselective synthesis of C -nucleoside analogues. Bench-stable ortho -isocyanophenyl thioglycosides can be converted to glycosyl radicals through rapid and efficient C-S bond homolysis when they are irradiated by visible light. The glycosyl radicals are subsequently trapped by the corresponding leaving group or other radical acceptors to provide diverse C -nucleoside analogues under mild conditions.