C6 substitution of inosine using hexamethylphosphorous triamide in conjunction with carbon tetrahalide or N-halosuccinimide

Eduardo A. Véliz, Peter A. Beal

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

Herein we report the facile conversion of 2',3',5'-tri-O- acetylinosine to three different nucleoside analogs via reaction of hexamethylphosphorous triamide and an organic halide. Acetyl-protected 6-bromopurine riboside, 6- chloropurine riboside and N6,N6-dimethyladenosine can each be prepared in good yield from 2',3',5'-tri-O-acetylinosine, HMPT and halide. The major product of the reaction is determined by the identity of the halide used and the reaction temperature. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1695-1697
Number of pages3
JournalTetrahedron Letters
Volume41
Issue number11
DOIs
StatePublished - Mar 11 2000
Externally publishedYes

Keywords

  • 6-halopurine
  • Halogenation
  • HMPT
  • Inosine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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