Novel stereocontrolled glycosidations of 2-deoxyglucopyranosyl fluoride using a heterogeneous solid acid, sulfated zirconia (SO₄[ZrO₂)

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-α-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.