Photoinitiated Thiol-ene Mediated Functionalization of 4,5-Enoses

Abstract

The photoinitiated thiol-ene reaction is emerging as a highly efficient methodology for thioglycoside synthesis. Herein, we report the first examples of the radical mediated hydrothiolation reaction of 4,5-unsaturated saccharides, offering efficient access to C4-position, S-linked glycosides. A diverse range of 4,5-unsaturated saccharides were investigated with high-yields achieved for the thioether products with complete regioselectivity and good diastereoselectivity. 1,2-Ethanedithiol products furnished a thiol-residue suitable for tagging and fluorescent labelling of a disaccharide.