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Nucleosides and Nucleotides. Part 17. A simple preparation of protected deoxynucleoside‐3'‐phosphates
Author(s) -
Bernardini Silvio,
Waldmeier Felix,
Tamm Christoph
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640719
Subject(s) - chemistry , reagent , triethylamine , nucleotide , nucleoside , combinatorial chemistry , ether , simple (philosophy) , chromatography , organic chemistry , stereochemistry , biochemistry , gene , philosophy , epistemology
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.