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Synthesis 1993; 1993(3): 303-306
DOI: 10.1055/s-1993-25853
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An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogenoacetates

Ratnakar R. Talekar* , Paul L. Coe, Richard T. Walker
  • *School of Chemistry, University of Birmingham Edgbaston, Birmingham, B15 2TT, England
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Publication Date:
17 September 2002 (online)

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A three-step reaction sequence starting from a ribonucleoside to give the corresponding 5′-O-acyl-2′,3′-didehydro-2′,3′-dideoxynucleoside is described. The key intermediate is the bromoacetate, made by reaction of the 2′,3′-methoxyethylidene nucleoside with acetyl bromide. Reductive elimination of the bromoacetate using a zinc-copper couple furnishes the desired compounds in good overall yield.