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, 1H 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.