Synlett 1999; 1999(6): 813-815
DOI: 10.1055/s-1999-2742
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Novel Stereocontrolled Glycosidations of 2-Deoxyglucopyranosyl Fluoride Using a Heterogeneous Solid Acid, Sulfated Zirconia (SO4/ZrO2)

Kazunobu Toshima* , Ken-ichi Kasumi, Shuichi Matsumura
  • *Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Further Information

Publication History

Publication Date:
31 December 1999 (online)

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.

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