Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds

Abstract

A transformation from the chair- into the boat conformation takes place when glucosides such as 1 are converted into glucosyl radicals 2. This preference for the boat conformation is due to the radical-stabilizing effect of the coplanar arrangement of the β-CO bond and semi-occupied orbital. The findings are of interest regarding stereoselective radical CC-linkage in the synthesis of C-glycosides.