Trifluoromethylation on a Nucleoside Sugar Scaffold: Design and Synthesis of 6'-Trifluoromethylcyclopentenyl-purine and -pyrimidine Nucleosides.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-07 Epub Date: 2025-02-26 DOI:10.1021/acs.orglett.5c00325

Jiyoon Song, Vikas R Aswar, Dnyandev B Jarhad, Lak Shin Jeong

引用次数: 0

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 (CF₃) 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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.