Novel Stereocontrolled Glycosidations of 2-Deoxyglucopyranosyl Fluoride Using a Heterogeneous Solid Acid, Sulfated Zirconia (SO4/ZrO2)

Abstract

Novel stereocontrolled glycosidations of a 2-deoxy-α-D-glucopyranosyl fluoride using a heterogeneous and environmentally friendly solid acid, sulfated zirconia (SO₄/ZrO₂), have been developed. The glycosidations of the perbenzylated 2-deoxy-α-D-glucopyranosyl fluoride 1 and various alcohols using SO₄/ZrO₂ in CH₃CN at 25 °C for 1 h predominantly gave the corresponding 2-deoxy-a-D-glucopyranosides. On the other hand, the corresponding 2-deoxy-β-D-glucopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO₄/ZrO₂ in the presence of molecular sieves 5A in Et₂O at 0 °C for 1 h.