Trifluoromethylationon a Nucleoside Sugar Scaffold:Design and Synthesis of 6′-Trifluoromethylcyclopentenyl-purineand -pyrimidine Nucleosides

Based on the promising biological activity of 6′-fluorocyclopentenyl-cytosine and -adenine, we report the design and synthesis of 6′-trifluoromethylcyclopentenyl-pyrimidine and -purine as potential antiviral agents. The introduction of a trifluoromethyl (CF<sub>3</sub>) group onto a sugar scaffold has been achieved using methyl fluorosulfonyldifluoroacetate (Chen’s reagent) as a key step. The resulting trifluoromethylated sugar intermediate provides an efficient pathway for synthesizing various nucleoside analogues, facilitating the expansion of structure–activity relationship studies for neplanocin A analogues.

Publication Details

Journal
Figshare
Published
2025-02-27
DOI
https://doi.org/10.1021/acs.orglett.5c00325.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Trifluoromethylationon a Nucleoside Sugar Scaffold:Design and Synthesis of 6′-Trifluoromethylcyclopentenyl-purineand -pyrimidine Nucleosides

Figshare
Fluorine in Organic Chemistry
article

Trifluoromethylationon a Nucleoside Sugar Scaffold:Design and Synthesis of 6′-Trifluoromethylcyclopentenyl-purineand -pyrimidine Nucleosides

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Abstract

Based on the promising biological activity of 6′-fluorocyclopentenyl-cytosine and -adenine, we report the design and synthesis of 6′-trifluoromethylcyclopentenyl-pyrimidine and -purine as potential antiviral agents. The introduction of a trifluoromethyl (CF<sub>3</sub>) group onto a sugar scaffold has been achieved using methyl fluorosulfonyldifluoroacetate (Chen’s reagent) as a key step. The resulting trifluoromethylated sugar intermediate provides an efficient pathway for synthesizing various nucleoside analogues, facilitating the expansion of structure–activity relationship studies for neplanocin A analogues.

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Fluorine in Organic Chemistry
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