Conversion of azidoamylose to ureidoamylose carbamates in one-pot reactions

In order to covert azidoamylose into ureidoamylose derivatives in a facile way, 6-azido-6-deoxyamylose was reacted with triphenylphosphine , and then with water and a phenyl isocyanate in turn. The obtained product was amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea), which was synthesized through three reactions in a one-pot method. The essential point to ensure the method be successful was that the water should be fed at an appropriate amount. The prepared amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea)s were characterized by FT-IR, 1 H NMR and elemental analysis , substantiating the reduction of the azido group and the subsequent derivatization of the resulted amino group and the hydroxyl group in amylose were fully performed. In addition, the amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea)s were coated on macroporous 3-aminopropyl silica gel to afford chiral stationary phases (CSPs) for high-performance liquid chromatography. The enantioseparations of the CSPs were evaluated, and the results indicated that the CSPs possessed chiral recognition ability towards some chiral compounds.