Synthesis of β-triphosphotriester pronucleotides

Yousef Beni, Chandravanu Dash, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

Abstract Dinucleoside phosphorochloridite was synthesized from phosphorus trichloride and three nucleoside analogs, 3′-fluoro-2′,3′-dideoxythymidine (FLT), 2′,3′-dideoxy-5-fluoro-3′-thiacytidine (FTC), and 2′,3′-dideoxy-3′-thiacytidine (3TC), in a multistep synthesis. Polymer-bound N-Boc p-acetoxybenzyl 5′-O-2′-deoxythymidine was reacted with dinucleoside phosphorochloridite in the presence of 2,6-lutidine, followed by the reaction with dodecyl alcohol and 5-(ethylthio)-1H-tetrazole, oxidation with tert-butyl hydroperoxide, and acidic cleavage, respectively, to afford the β-triphosphotriester derivatives containing three different nucleosides.

Original languageEnglish (US)
Article number46039
Pages (from-to)2247-2250
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number17
DOIs
StatePublished - Apr 22 2015
Externally publishedYes

Keywords

  • Fatty chains
  • Nucleosides
  • Nucleotides
  • Pronucleotides
  • Triphosphotriesters

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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