Synlett p. 643 - 645 (1998)
Update date:2022-08-03
Topics:
Toshima, Kazunobu
Kasumi, Ken-Ichi
Matsumura, Shuichi
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 5A? in Et2O at 25°C for 15 h.
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