Nucleosides and Nucleotides. Part 17. A Simple Preparation of Protected Deoxynucleoside-3'-phosphates

Article abstract of DOI:10.1002/hlca.19810640719

A simple method for the preparation of fully protected 2'-deoxynucleoside-3'-phosphates is described.The main step, phosphorylation of partially protected deoxynucleosides, is performed with the monofunctional reagent p-chlorophenyl(2-cyanoethyl)phosphochloridate (2) in dioxane.This reagent is quickly prepared from readily accessible p-chlorophenyl phosphodichloridate by reaction with 3-hydroxypropionitrile and triethylamine in dioxane or ether.The crude reagent is used directly for phosphorylation.After chromatography, protected deoxynucleoside-3'-phosphonates were isolated in yields of 80-87percent .The method described here, which has been optimized in detail, represents a simple alternative to published methods.