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Nucleosides and Nucleotides. Part 17. A simple preparation of protected deoxynucleoside-3'-phosphates

✍ Scribed by Silvio Bernardini; Felix Waldmeier; Christoph Tamm

Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 415 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640719

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✦ Synopsis

Abstract

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^3^) (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′‐phosphates were isolated in yields of 80–87%. The method described here, which has been optimized in detail, represents a simple alternative to published methods.

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