Synthesis of Highly Pure Enantiomers of the Insecticide Salithion

Shao Yong Wu, Akinori Hirashima, Morifusa Eto, Kazunori Yanagi, Eriko Nishioka, Koichi Moriguchi

Research output: Contribution to journalArticle

Abstract

Optically active salithion (>98% e.e.) was obtained via an L-proline methyl ester derivative (PS), whose diastereomers were easily separated, with subsequent sulfuric acid-catalyzed methanolysis. The configuration of each diastereomeric PS was determined by NMR and single-crystal X-ray analysis. The optical purity of each PS and of the salithion enantiomers was measured by 1H-NMR and HPLC, respectively. The sulfuric acid-catalyzed methanolysis of PS to salithion was confirmed to have proceeded with an inversion of the configuration at the phosphorus atom by an experiment using model compounds.

Original languageEnglish
Pages (from-to)157-163
Number of pages7
JournalAgricultural and Biological Chemistry
Volume53
Issue number1
DOIs
Publication statusPublished - Jan 1 1989

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methanolysis
Enantiomers
enantiomers
sulfuric acid
Insecticides
insecticides
diastereomers
synthesis
Nuclear magnetic resonance
purity
crystals
proline
X-radiation
chemical derivatives
esters
X ray analysis
Proline
phosphorus
Phosphorus
Esters

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

Cite this

Synthesis of Highly Pure Enantiomers of the Insecticide Salithion. / Wu, Shao Yong; Hirashima, Akinori; Eto, Morifusa; Yanagi, Kazunori; Nishioka, Eriko; Moriguchi, Koichi.

In: Agricultural and Biological Chemistry, Vol. 53, No. 1, 01.01.1989, p. 157-163.

Research output: Contribution to journalArticle

Wu, Shao Yong ; Hirashima, Akinori ; Eto, Morifusa ; Yanagi, Kazunori ; Nishioka, Eriko ; Moriguchi, Koichi. / Synthesis of Highly Pure Enantiomers of the Insecticide Salithion. In: Agricultural and Biological Chemistry. 1989 ; Vol. 53, No. 1. pp. 157-163.
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