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

GRAPHICAL ABSTRACT

ABSTRACT

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 ¹H, ¹³C, ¹⁹F, ³¹P NMR, and ESI MS spectroscopy.

KEYWORDS:

• Arbuzov reaction
• fluorinated sugar phosphonates
• fluorinated sugar phosphoramidates
• neighboring group participation

Funding

This work was financed by the National Science Centre (grant SONATA 4 - 2012/07/D/ST5/02303).