Novel Stereocontrolled Glycosidations Using a Solid Acid, SO4/ZrO2, for Direct Syntheses of α- and β-Mannopyranosides
- 1 June 1998
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1998 (6) , 643-645
- https://doi.org/10.1055/s-1998-1741
Abstract
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.Keywords
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