SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS: A REGIOSELECTIVE ADDITION OF THE PRIMARY HYDROXYL OF MONOSACCHARIDES TO ALKYLISOCYANATES

Article abstract of DOI:10.1016/S0040-4039(00)95568-0

The primary hydroxyl groups of D-glucose, D-galactose and methyl-α-D-glucoside add selectively to alkylisocyanates, thus affording respectively 6-O-carbamoyl-D-glycopyranoses and methyl-6-O-carbamoyl-α-D-glucopyranosides with high yields (except for galactosyl compounds), the temporary protection of the other hydroxyls of the starting sugars being not necessary in the present case.