Synthesis of isotopically labeled 1,3-dithiane.
J Labelled Comp Radiopharm
; 57(5): 338-41, 2014 May 15.
Article
em En
| MEDLINE
| ID: mdl-24861982
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.
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Base de dados:
MEDLINE
Assunto principal:
Quinolizinas
/
Compostos de Enxofre
/
Isótopos de Carbono
Idioma:
En
Revista:
J Labelled Comp Radiopharm
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Estados Unidos