Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives

Toshiyuki Kaneko, Mariko Aso, Noboru Koga, Hiroshi Suemune

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19 Citations (Scopus)

Abstract

(Chemical Equation Presented) 2′-Deoxyribofuranosylpurine derivatives bearing an N-tert-butylaminoxyl group (1a and 2a) were synthesized via oxidation of the corresponding N-tert-butylhydroxylamines (1b and 2b), which were synthesized by lithiation of 8-TIPS-6-chloropurine (3) at the 2-position and the following reaction with 2-methyl-2-nitrosopropane. Treatment of 1b and 2b with 1 equiv of NalO4 resulted in efficient formation of 1a and 2a, which were isolated as purple and red solids, respectively. The EPR spectra of 1a showed pH dependency due to structural change of purine moiety.

Original languageEnglish
Pages (from-to)303-306
Number of pages4
JournalOrganic Letters
Volume7
Issue number2
Publication statusPublished - Jan 20 2005

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kaneko, T., Aso, M., Koga, N., & Suemune, H. (2005). Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives. Organic Letters, 7(2), 303-306.