Synthesis of a conformationally locked version of puromycin amino nucleoside

Yongseok Choi, Clifford George, Peter Strazewski, Victor E. Marquez

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

(formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.

Original languageEnglish
Pages (from-to)589-592
Number of pages4
JournalOrganic Letters
Volume4
Issue number4
DOIs
Publication statusPublished - 2002 Feb 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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