Synthesis of nucleoside epoxyphosphonates

Article abstract of DOI:10.1016/0040-4020(96)00684-9

Reaction of two regioisomeric uridine derivatives, 1-[3-(diethoxyphosphinyl)-5-O-trityl-β-D-xylofuranosyl]uracil (4) and 1-[2-(diethoxyphosphinyl)-5-O-trityl-β-D-arabinofuranosyl]uracil (13), with triflyl chloride and 4-pyrrolidinopyridine (4-PDP) results in formation of the corresponding nucleoside epoxyphosphonates. This transformation is immediately useful for confirming the trans relationship of the 2'- and 3'-hydroxyl groups in the geminal hydroxyphosphonates 3 and 12, and provides access to two new families of nucleoside derivatives that may be of interest for their synthetic utility and biological properties.