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.
ASJC Scopus subject areas
- Organic Chemistry