Synthesis and Characterization of N-(O,O-Dialkyl Phosphoryl)-D-glucosamine

Abstract

Using D-glucosamine hydrochloride as a starting material and alkylphosphite as the phosphorylating agent, a new analogue of glycosyl phosphate, namely N-(O, O-dialkyl phosphoryl)-D-glucosamine, was synthesized without hydroxyl protection by Atherton–Todd reaction. The structure of N-(O, O-dialkyl phosphoryl)-D-glucosamine was determined by FT-IR, ¹H NMR, ¹³C NMR, ³¹P NMR, and HR MS. This concise and convenient synthetic pathway provides a new approach for the preparation of N-phosphoryl glucosamine derivatives.

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Keywords:

• Characterization
• N-(O,O-dialkyl phosphoryl)-D-glucosamine
• glucosamine

Acknowledgments

The authors would like to thank the Chinese National Science Foundation (No. 20872134) for their financial support.