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Synthesis of isotopically labeled 1,3-dithiane
Rodolfo A Martinez1, David R Glass, Erick G Ortiz
1Bioscience 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.
Journal of Labelled Compounds & Radiopharmaceuticals
|May 28, 2014
Summary
Stable isotopomers of 1,3-dithiane, including radiolabeled versions, can be synthesized efficiently. This method utilizes readily available starting materials like methanol and water for creating labeled synthons.
Area of Science:
- Organic Chemistry
- Isotope Chemistry
Background:
- 1,3-dithiane serves as a protected formaldehyde anion equivalent.
- Labeled synthons are valuable in chemical synthesis and research.
Purpose of the Study:
- To develop a facile synthesis for stable isotopomers of 1,3-dithiane.
- To enable the preparation of radiolabeled 1,3-dithianes.
Main Methods:
- Synthesis of [(13)C]methyl phenyl sulfide from [(13)C]methanol.
- Oxidation to [(13)C]methyl phenyl sulfoxide.
- Deuterium exchange with (2)H2O to yield [(13)C, (2)H3]methyl phenyl sulfoxide.
- Conversion to 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane.
Main Results:
- A two-step synthesis for 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane was achieved.
- All possible C2 stable isotopomers of 1,3-dithiane are accessible.
- The synthetic route is adaptable for radiolabeled 1,3-dithianes.
Conclusions:
- A versatile and efficient method for synthesizing isotopically labeled 1,3-dithianes has been established.
- This approach broadens the availability of labeled synthons for various applications.
- The described synthesis is amenable to the preparation of radiolabeled compounds.
