Synthesis of perdeuterated analogues of the epoxide metabolites of butadiene: 1,2-epoxybut-3-ene-d6 and 1,2,3,4-diepoxybutane-d6

R. Sangaiah, N. I. Christova-Gueorguieva, A. Ranasinghe, N. Yu Tretyakova, A. Gold, L. M. Ball, J. A. Swenberg

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Abstract

Deuterated analogues of the carcinogenic metabolites of 1,3-butadiene (ED) 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-d6 with appropriate quantities of dimethyldioxirane (DMDO). Both epoxides were characterized by proton and deuterium NMR and mass spectrometry; yields were quantitated by gas chromatography/mass spectrometry using samples of known concentrations of commercially available non-deuterated epoxides as standards. The synthesized DEB-d6 was a mixture of the enantiomeric RR and SS enantiomers and the meso RS diastereomers.

Original languageEnglish (US)
Pages (from-to)731-739
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume39
Issue number9
DOIs
StatePublished - Sep 1 1997

Keywords

  • 1,2,3,4-Diepoxybutane-d
  • 1,2-Epoxybut-3-en-d
  • 1,3-Butadiene
  • 1,3-Butadiene-d
  • Dimethyldioxirane oxidation

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