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Synlett 1998; 1998(6): 643-645
DOI: 10.1055/s-1998-1741
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Novel Stereocontrolled Glycosidations Using a Solid Acid, SO4/ZrO2, for Direct Syntheses of α- and β-Mannopyranosides

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, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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Novel stereocontrolled glycosidations using an environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), for direct syntheses of α- and β-mannopyranosides have been developed. The glycosidations of the totally benzylated mannopyranosyl fluoride 1 and various alcohols using SO4/ZrO2 in CH3CN at 40 °C for 15 h exclusively gave the corresponding α-mannopyranosides. On the other hand, the corresponding β-mannopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5 Å in Et2O at 25 °C for 15 h.

glycosidation - carbohydrates - mannopyranoside - solid acid - sulfated zirconia