Download PDF
Synlett 1998; 1998(6): 643-645
DOI: 10.1055/s-1998-1741
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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