Stereoselective Hydrolysis of p-Nitrophenyl Glycoside by Boronic Acid

The alkaline hydrolysis of p-nitrophenyl α-D-glucoside, α-D-galactoside, and β-D-mannoside was selectively accelerated by addition of methyl boronic acid, as compared to that of the corresponding β-D-glucoside, β-D-galactoside, and α-D-mannoside. In the case of p-nitrophenyl α (or β)-D-glucoside, the α/β selectivity was increased up to 110 when four molar equivalents of methyl- or phenylboronic acid were added.