Stereoselective hydrolysis of p-nitrophenyl glycoside by boronic acid

Authors
Ohe, T Kida, T Zhang, WB Nakatsuji, Y Ikeda, I
Citation
T. Ohe et al., Stereoselective hydrolysis of p-nitrophenyl glycoside by boronic acid, CHEM LETT, (11), 1998, pp. 1077-1078
Citations number
13
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
11
Year of publication
1998
Pages
1077 - 1078
Database
ISI
SICI code
0366-7022(199811):11<1077:SHOPGB>2.0.ZU;2-7
Abstract
The alkaline hydrolysis of p-nitrophenyl alpha-D-glucoside, alpha-D-galacto side, and beta-D-mannoside was selectively accelerated by addition of methy l boronic acid, as compared to that of the corresponding beta-D-glucoside, beta-D-galactoside, and alpha-D-mannoside. In the case of p-nitrophenyl a ( or beta)-D-glucoside, the alpha/beta selectivity was increased up to 110 wh en four molar equivalents of methyl- or phenylboronic acid were added.