Premium
Synthesis of perdeuterated analogues of the epoxide metabolites of butadiene: 1,2‐epoxybut‐3‐ene‐d 6 and 1,2,3,4‐diepoxybutane‐d 6
Author(s) -
Sangaiah R.,
ChristovaGueorguieva N. I.,
Ranasinghe A.,
Tretyakova N. Yu.,
Gold A.,
Ball L. M.,
Swenberg J. A.
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199709)39:9<731::aid-jlcr20>3.0.co;2-e
Subject(s) - chemistry , dimethyldioxirane , deuterium , mass spectrometry , epoxide , enantiomer , diastereomer , ene reaction , 1,3 butadiene , stereochemistry , organic chemistry , chromatography , catalysis , physics , quantum mechanics
Deuterated analogues of the carcinogenic metabolites of 1,3‐butadiene (BD) 1,2‐epoxybut‐3‐ene (EB) and 1,2,3,4‐diepoxybutane (DEB), which are not commercially available, are conveniently synthesized in good yields by oxidation of BD‐d 6 with appropriate quantities of dimethyldioxirane (DMDO). Both epoxides were characterized by proton and deuterium NMR and mass spectrometry; yields were quantified by gas chromatography/mass spectrometry using samples of known concentrations of commercially available non‐deuterated epoxides as standards. The synthesized DEB‐d 6 was a mixture of the enantiomeric RR and SS enantiomers and the meso RS diastereomers. © 1997 John Wiley & Sons, Ltd.