“Boomerang” Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of <i>C</i>-Glycosylated Benzothiazoles from <i>ortho</i>-Isocyanophenyl Thioglycosides

Abstract

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.

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