Journal
SYNLETT
Volume 28, Issue 15, Pages 2014-2017Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588445
Keywords
nucleoside synthesis; Mitsunobu reaction; N-glycosidation; stereoselectivity; solvent effects
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Funding
- JSPS KAKENHI [15H01062, 15K13738, 26288075]
- Grants-in-Aid for Scientific Research [26288075, 15H01062, 15K13738] Funding Source: KAKEN
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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 was systematically studied. The effect of phosphine, azodicarbonyl reagent, and solvent on the product yield and alpha/beta ratio was investigated, and the highest yield and beta-selectivity were obtained using (n-Bu) 3P and 1,1'-(azodicarbonyl) dipiperidine in DMF. The reaction was successfully applied to various nucleobase analogues.
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