Practical Synthesis of Sugar Monophosphonucleotides

Abstract

A reliable procedure for the preparation of sugar nucleoside monophosphates is presented, which involves condensation of an activated glycosyl‐1‐H‐phosphonate with an appropriately protected nucleoside and simple end‐product isolation via lithium perchlorate–induced precipitation. The utility of these methods is demonstrated by the preparation of a number of purine‐ and pyrimidine‐based sugar nucleoside monophosphate derivatives.

Keywords:

• acyl deprotection
• glycosyl‐1‐H‐phosphonates
• sugar nucleotides

Acknowledgments

This work was supported by a Wellcome Trust Showcase Award (grant ref. 067525/Z/02/Z). We also thank the Engineering and Physical Sciences Research Council (EPSRC) Mass Spectrometry Service Centre, Swansea, for invaluable support.