NOVEL STEREOCONTROLLED GLYCOSIDATIONS USING A SOLID ACID, SO4 ZRO2, FOR DIRECT SYNTHESES OF ALPHA-MANNOPYRANOSIDES AND BETA-MANNOPYRANOSIDES/

Authors
TOSHIMA K KASUMI K MATSUMURA S
Citation
K. Toshima et al., NOVEL STEREOCONTROLLED GLYCOSIDATIONS USING A SOLID ACID, SO4 ZRO2, FOR DIRECT SYNTHESES OF ALPHA-MANNOPYRANOSIDES AND BETA-MANNOPYRANOSIDES/, Synlett, (6), 1998, pp. 643
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
6
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):6<643:NSGUAS>2.0.ZU;2-5
Abstract
Novel stereocontrolled glycosidations using an environmentally friendl y solid acid, sulfated zirconia (SO4/ZrO2), for direct syntheses of al pha- and beta-mannopyranosides have been developed. The glycosidations of the totally benzylated mannopyranosyl fluoride 1 and various alcoh ols using SO4/ZrO2 in CH3CN at 40 degrees C for 15 h exclusively gave the corresponding alpha-mannopyranosides. On the other hand, the corre sponding beta-mannopyranosides were selectively obtained by the glycos idations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5 Angstrom in Et2O at 25 degrees C for 15 h.