Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism

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Abstract

Fluorinated nucleoside analogues have attracted much attention as anticancer and antiviral agents and as probes for enzymatic function. However, the lack of direct synthetic methods, especially for 2′,3′-dideoxy-2′,3′-difluoro nucleosides, hamper their practical utility. In order to design more efficient synthetic methods, a better understanding of the conformation and mechanism of formation of these molecules is important. Herein, we report the synthesis and conformational analysis of a 2′,3′-dideoxy-2′,3′-difluoro and a 2′-deoxy-2′-fluoro uridine derivative and provide an insight into the reaction mechanism. We suggest that the transformation most likely diverges from the SN1 or SN2 pathway, but instead operates via a neighbouring-group participation mechanism.
Original languageEnglish
Article number5513
Number of pages13
JournalMolecules
Volume25
Issue number23
DOIs
Publication statusPublished - 25 Nov 2020

Keywords

  • Nucleoside
  • Fluorine
  • Fluorination
  • Neighbouring-group participation
  • Mechanism

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