Preparation and condensation of D-glucopyranose N-phenylcarbamates and N-methyl-N-phenylcarbamates

Abstract A number of tri- and tetra-( N -phenylcarbamate) and - N -methyl- N -phenyl-carbamate derivatives of methyl α- D -glucopyranoside were prepared and found resistant to acid hydrolysis. Alcoholysis and hydrolysis of the corresponding derivatives of cellulose gave oligomeric products and some loss of protecting groups. The fully substituted derivatives of benzyl β- D -glucopyranoside were resistant to hydrogenolysis. D -Glucopyranose 2,3,4-tri-( N -phenylcarbamate) and -( N -methyl- N -phenylcarbamate) were prepared from 1,6-anhydro-β- D -glucopyranose and, on treatment with phosphoric anhydride, gave in the first case a crosslinked polymer with a small percent of phosphorus and in the second one a monomeric diphosphate. Although carbanilates are able to act as participating groups, the reported method for polymerizing D -glucopyranose 2,3,6-tri- O -( N -phenylcarbamate) is not general for closely related compounds.