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Synthesis 2004(6): 960-966  
DOI: 10.1055/s-2004-815997
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

General Method for the Synthesis of Chiral 2,3-Bisarylmethoxy-1,4-Butanediols from l-(+)-Tartrate

Riichiro Tsuji, Shigeru Arai, Atsushi Nishida*
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Fax: +81(43)2902909; e-Mail: nishida@p.chiba-u.ac.jp;
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Publication History

Received 28 November 2004
Publication Date:
04 March 2004 (online)

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Abstract

Various (2S,3S)-2,3-bisarylmethoxy-1,4-butanediols 3a-h were synthesized from l-(+)-tartrate through bisallylether 12. Protection of the primary alcohol as an allyl ether was essential for selective deprotection in the presence of reactive arylmethyl ethers.

Key words

tartaric acid - allyl ether - catalyst - palladium - deprotection