The mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives

[GRAPHICS] The conversion of methyl carbamate to the corresponding free amine is descr ibed for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 deg rees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the pr esence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affor ds selectively, orthogonal N-deprotected carbohydrates.