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

Toshiyuki Kaneko, Mariko Aso, Noboru Koga, Hiroshi Suemune

Research output: Contribution to journalArticle

18 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

Fingerprint

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

Cite this

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.

In: Organic Letters, Vol. 7, No. 2, 20.01.2005, p. 303-306.

Research output: Contribution to journalArticle

Kaneko, T, Aso, M, Koga, N & Suemune, H 2005, 'Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives', Organic Letters, vol. 7, no. 2, pp. 303-306.
Kaneko, Toshiyuki ; Aso, Mariko ; Koga, Noboru ; Suemune, Hiroshi. / Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives. In: Organic Letters. 2005 ; Vol. 7, No. 2. pp. 303-306.
@article{547e4c70250e454da07ea9999029abc1,
title = "Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives",
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.",
author = "Toshiyuki Kaneko and Mariko Aso and Noboru Koga and Hiroshi Suemune",
year = "2005",
month = "1",
day = "20",
language = "English",
volume = "7",
pages = "303--306",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives

AU - Kaneko, Toshiyuki

AU - Aso, Mariko

AU - Koga, Noboru

AU - Suemune, Hiroshi

PY - 2005/1/20

Y1 - 2005/1/20

N2 - (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.

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.

UR - http://www.scopus.com/inward/record.url?scp=13444306471&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=13444306471&partnerID=8YFLogxK

M3 - Article

VL - 7

SP - 303

EP - 306

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 2

ER -