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Communication | Regular issue | Vol 41, No. 6, 1995, pp.1131-1134
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7068
A General and Efficient Synthesis of Optically Pure S-Arylmercapturates

Shizuo Nakamura*, Mitsuyoshi Kondo, Kiyoto Goto, Shinsaku Naito, Yoshiaki Tsuda, and Kozo Shishido*

*Institute for Medicinal Resources, University of Tokushima, Sho-machi 1, Tokushima 770, Japan

Abstract

Optically pure S-arylmercapturate derivatives (4a-d) were efficiently synthesized via the reaction of Boc-L-Ser-OMe (6) with a variety of disulfides (5a-d) in the presence of tri-n-butylphosphine. The procedure was successfully applied to the synthesis of the enantiomerically pure S-thienylmercapturic acid (2), a metabolite of antiinflammatory drug DUP697 (1).