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A Systematic Study of the Synthesis of 2ʹ-Deoxynucleosides by Mitsunobu Reaction

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The Mitsunobu reaction has emerged as an important alternative for the preparation of synthetic 2′-deoxynucleosides, which have various biological and biotechnological applications. In this work, the Mitsunobu-based synthesis of 2′-deoxynucleosides… Click to show full abstract

The Mitsunobu reaction has emerged as an important alternative for the preparation of synthetic 2′-deoxynucleosides, which have various biological and biotechnological applications. In this work, the Mitsunobu-based synthesis of 2′-deoxynucleosides was systematically studied. The effect of phosphine, azodicarbonyl reagent, and solvent on the product yield and α/β ratio was investigated, and the highest yield and β-selectivity were obtained using ( n -Bu) 3 P and 1,1′-(azodicarbonyl)dipiperidine in DMF. The reaction was successfully applied to various nucleobase analogues.

Keywords: study synthesis; mitsunobu reaction; reaction; synthesis deoxynucleosides; systematic study

Journal Title: Synlett
Year Published: 2017

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