Synthesis of isotopically labeled 1,3-dithiane

J Labelled Comp Radiopharm. 2014 May 15;57(5):338-41. doi: 10.1002/jlcr.3185. Epub 2014 Feb 7.

Abstract

The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane in two steps from [(13)C]- or [(13) C, (2)H3 ]methyl phenyl sulfoxide. We have previously reported the high yield synthesis of [(13)C]methyl phenyl sulfide from [(13)C]MEOH and the oxidation of [(13)C]methyl phenyl sulfide to [(13)C]methyl phenyl sulfoxide. Here, we describe the facile exchange of deuterium from (2) H2 O into [(13)C]methyl phenyl sulfoxide to yield [(13)C, (2)H3]methyl phenyl sulfoxide. Thus, from [(13)C]MEOH and (2)H2O, all possible C2 stable isotopomers of 1,3-dithiane are available. Our synthetic route is also amenable to preparation of radiolabeled 1,3-dithianes.

Keywords: 13C-labeled synthons; stable isotope labeling.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes / chemical synthesis*
  • Carbon Isotopes / isolation & purification*
  • Isotope Labeling / methods
  • Quinolizines / chemical synthesis*
  • Quinolizines / isolation & purification*
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / isolation & purification
  • Sulfur Compounds / chemical synthesis*
  • Sulfur Compounds / isolation & purification*

Substances

  • Carbon Isotopes
  • Quinolizines
  • Radiopharmaceuticals
  • Sulfur Compounds
  • dithiane