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

Toshiyuki Kaneko, Mariko Aso, Noboru Koga, Hiroshi Suemune

研究成果: ジャーナルへの寄稿記事

18 引用 (Scopus)

抄録

(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.

元の言語英語
ページ(範囲)303-306
ページ数4
ジャーナルOrganic Letters
7
発行部数2
出版物ステータス出版済み - 1 20 2005

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Bearings (structural)
purines
Paramagnetic resonance
Derivatives
Oxidation
oxidation
synthesis
purine
6-chloropurine
tert-nitrosobutane
N-tert-butylhydroxylamine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

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.

Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives. / Kaneko, Toshiyuki; Aso, Mariko; Koga, Noboru; Suemune, Hiroshi.

:: Organic Letters, 巻 7, 番号 2, 20.01.2005, p. 303-306.

研究成果: ジャーナルへの寄稿記事

Kaneko, T, Aso, M, Koga, N & Suemune, H 2005, 'Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives', Organic Letters, 巻. 7, 番号 2, pp. 303-306.
Kaneko, Toshiyuki ; Aso, Mariko ; Koga, Noboru ; Suemune, Hiroshi. / Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives. :: Organic Letters. 2005 ; 巻 7, 番号 2. pp. 303-306.
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AB - (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.

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