Synthesis of vinylic C-glycosides from telluroglycosides. Addition of photochemically and thermally generated glycosyl radicals to alkynes

Article abstract of DOI:10.1016/S0040-4039(99)00182-3

Glycosyl radicals generated from telluroglycosides react with a variety of alkynes to give the corresponding vinylic C-glycosides in good to excellent yields. The reaction takes place in an atom transfer manner to form vinyl telluride, and the resulting C-Te bond is transmetalated to the C-Zn bond with Et₂Zn or reduced to the C-H bond with tributyltin hydride.