Nucleosides. CXLIV. Some Reactions of 2-0-Triflyl-2,3’-anhydroxylosyluracil with Nucleophilic Reagents. Synthesis of 2‘-Chloro-2’,3’-dideoxyuridinene. Studies Directed toward the Synthesis of 2‘-Deoxy-2’-substituted arabino Nucleosides. (5)

Krzysztof W. Pankiewicz, Kyoichi A. Watanabea

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Treatment of ‘-anhydro-4-(5-0-acety1-2-0-triflyl-fl-D-xylofuranosyl)uracil β-D-xylofuranosyluracil with LiCl in hexamethylphosphoric triamide afforded the 2’-“up” chloride of the anhydronucleoside, i.e. 2’-triflate group was directly displaced by the chloride nucleophile. All attempts to hydrolyze the 2,3’-anhydro linkage resulted in the formation of 2’-chloro-2’,3’-didehydro-dideoxynucleoside.

Original languageEnglish (US)
Pages (from-to)4498-4502
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume35
Issue number11
DOIs
StatePublished - 1987

Keywords

  • 3-didehydro-2
  • 3-dideoxy-β ~
  • 3’-anhydro-l-(2-0- triflyl-β
  • 3’-anhydro-l-(2-chloro-2-deoxy-β
  • 3’-dideoxyuridinene
  • D-glyceropento-2-enofuranosyl)uracil 2’-chloro-2’
  • D-lyxofuranosyl)uracil l-(2-chloro-2
  • D-xylofuranosyl)uracil 2
  • nucleoside anhydronucleoside reaction mechanism 2

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