JOURNAL 768


Organic Communications
VOLUME & ISSUE
Year: 2015 Issue: 1 January-March
PAGES
p.9 - 16
STATISTICS
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AUTHORS
    Joanna Nizioł, Wojciech Rode and Tomasz Ruman
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GRAPHICAL ABSTRACT


ABSTRACT


A novel synthetic approach is presented, involving unsaturated nucleoside hydroboration, with protected stavudine catalytically boronated with pinacolborane to several pinacolborane derivatives of stavudine or 2’,3’-dideoxythymidine. The products were converted to much more stable trifluoroborate derivatives that may be considered trifluoroboron analogues of nucleoside phosphates. The post-reaction mixture contained four isomers, being products of catalytic hydroboration, and two isomers, resulting from dehydrogenative borylation, each containing unsaturated 2’,3’-moiety. The new compounds were analyzed with NMR and LDI-HRMS methods.

KEYWORDS
  • BNCT
  • boron nucleoside
  • boron nucleotide
  • dehydrogenative borylation
  • hydroboration
  • NMR