Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine derivatives.
[Structure: see text] 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 NaIO4 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.
Kaneko
Toshiyuki
T
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
Aso
Mariko
M
Koga
Noboru
N
Suemune
Hiroshi
H
D000588:Amines / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D006863:Hydrogen-Ion Concentration; D008094:Lithium / Q000737:chemistry; D010084:Oxidation-Reduction; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry*
D000588:Amines; D002073:Butanes; D011687:Purines; C046888:butane; D008094:Lithium