1. Synthesis of 2′-deoxynucleoside analogs from thioglycosides
- Author
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V. I. Shvets, A. I. Davydova, A. M. Yurkevich, E. N. Savvateeva, Yu. G. Kirillova, G. D. Gungarova, A. S. Arkhipova, and A. I. Lyutik
- Subjects
Pharmacology ,Solvent ,chemistry.chemical_compound ,Chemistry ,Stereochemistry ,Yield (chemistry) ,Drug Discovery ,Condensation ,Pharmacology toxicology ,Stereoselectivity ,Thymine - Abstract
The synthesis of pharmacologically active 2′-deoxynucleoside analogs, namely 2′,3′-dideoxythymidine (I) and 2′,3′-dideoxy-3′-fluorothymidine (II), is described. The proposed approach consists in condensation of the corresponding thioglycosides with silylated thymine using N-bromosuccinimide as a promoter. In the case of compound II, it is shown that the yield and stereoselectivity of this process depend on the equivalent ratio of silylated base and solvent.
- Published
- 2006
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