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Competing interests during the key -glycosylation of 6-chloro-7-deaza-7-iodopurine for the synthesis of 7-deaza-2'-methyladenosine using Vorbrüggen conditions. | LitMetric

AI Article Synopsis

  • A concise 3-step method to synthesize the antiviral compound 7DMA is outlined.
  • The study investigates a significant by-product formed during the reaction involving specific glycosylation conditions, revealing that the solvent can become a reactive competitor.
  • These insights suggest a need to adjust reaction protocols when using weakly reactive nucleobases with Lewis acids, and the final 7DMA compound was tested against a new flavivirus.

Article Abstract

A short 3-step synthesis of the antiviral agent 7DMA is described herein. The nature of a major by-product formed during the key -glycosylation of 6-chloro-7-deaza-7-iodopurine with perbenzoylated 2-methyl-ribose under Vorbrüggen conditions was also investigated. Spectroscopic analyses support that the solvent itself is converted into a nucleophilic species competing with the nucleobase and further reacting with the activated riboside in an unanticipated fashion. These findings call for a revision of reaction conditions when working with weakly reactive nucleobases in the presence of Lewis acids. 7DMA thus obtained was evaluated for its efficacy against an emerging flavivirus .

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10076608PMC
http://dx.doi.org/10.3389/fchem.2023.1163486DOI Listing

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