2′-Deoxy-2′-C-trifluoromethyl β-D-Ribonucleoside Analogues: Synthesis and Antiviral Evaluations
✍ Scribed by Frederic Jeannot; Gilles Gosselin; Christophe Mathe
- Publisher
- John Wiley and Sons
- Year
- 2004
- Weight
- 55 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0931-7597
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## Abstract The synthesis of the 3‐ and 4‐(methylthio)pyrazolo[3,4‐__d__]pyrimidine N^1^‐ and N^2^‐2′‐deoxy‐β‐D‐ribonucleosides 2b, 15 is described. Anionic glycosylation of 5‐amino‐3‐(methylthio)‐4‐pyrazolecarbonitrile (4) or 4‐(methylthio)pyrazolo[3,4‐__d__]pyrimidine (12) with 2‐deoxy‐3,5‐di‐__O
## Abstract Nucleobase‐anion glycosylation of 6‐(methylthio)‐2‐azapurine (1) with 2‐deoxy‐3,5‐di‐__O__‐(p‐toluoyl)‐α‐D‐erythro‐pentofuranosyl chloride (2) yields the 2′‐deoxy‐β‐D‐ribofuranosides 3–5 stereoselectively. The distribution of regioisomers is as follows: N‐9 (32%); N‐2 (30%), and N‐7 (7%