The synthesis of new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks in the synthesis of modified hyaluronic acid subunits

The synthesis of several new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks for the synthesis of modified hyaluronic acid subunits is described. These compounds were prepared from d-glucose and d-glucosamine hydrochloride. The syntheses of phosphonates and phosphoramidates are based on arbuzov and staudinger reactions. The products were fully characterized by H-1, C-13, F-19, P-31 NMR, and ESI MS spectroscopy.