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Updated: Jun 17, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Synthesis of 3'-deoxy-4'-thionucleosides
Yoshihiro Natori1, Aya Itoh1, Momoko Adachi1
1Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Komatsushima 4-4-1, Aoba-ku, Sendai, 981-8558, Japan. yoshimura@tohoku-mpu.ac.jp.
None:
The racemic synthesis of 3'-deoxy-4'-thionucleosides, which are of interest as potential antiviral and antitumor drug candidates, was achieved. A key reaction involved a tandem intra- and intermolecular SN2 reaction of a thioepoxide for constructing a 3'-deoxy-4'-thioribose skeleton. Pummerer reaction and subsequent Vorbrüggen-type glycosylation furnished 3'-deoxy-4'-thionucleosides. The proposed method is applicable for enantioselective synthesis using a commercially available chiral oxirane derivative.
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