Convenient synthesis of glycosyl bromide from 1-O-acetyl sugars by photo-irradiative phase-vanishing reaction of molecular bromine

摘要

The synthesis of glycosyl bromides from 1-O-acetyl sugars using a photo-irradiative phase-vanishing method involving molecular bromine was achieved. A bottom phase of molecular bromine was overlaid first with perfluorohexanes (FC-72), followed by overlaying with ethyl acetate containing a 1-O-acetyl sugar. Upon irradiation, the bromine layer gradually disappeared, leaving two phases. Glycosyl bromide was obtained in good yield from the ethyl acetate phase.