2. Academic Validation
  3. Synthesis of isotopically labeled 1,3-dithiane

Synthesis of isotopically labeled 1,3-dithiane

  • J Labelled Comp Radiopharm. 2014 May 15;57(5):338-41. doi: 10.1002/jlcr.3185.
Rodolfo A Martinez 1,  David R Glass,  Erick G Ortiz,  Marc A Alvarez,  Clifford J Unkefer
Affiliations

Affiliation

  • 1 Bioscience Division, Los Alamos National Laboratory, The National Stable Isotope Resource, MS E529, Los Alamos, NM, 87545, USA; Department of Chemistry, New Mexico Highlands University, Box 9000, Las Vegas, NM, 87701, USA.
PMID: 24861982 DOI: 10.1002/jlcr.3185
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.

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