Large Laboratory Scale Synthesis of (2S, 3S)-2-(4-Methoxybenzyloxy)-3, 4-O-(3-pentylidene)-1, 3, 4-butantriol, a Versatile Chiral Building Block in Natural Product Synthesis

Kiyoshi HORITA; Youji SAKURAI; Shun-ichiro HACHIYA; Masaaki NAGASAWA; Osamu YONEMITSU

doi:10.1248/cpb.42.683

Kiyoshi HORITA, Youji SAKURAI, Shun-ichiro HACHIYA, Masaaki NAGASAWA, Osamu YONEMITSU

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Keywords: chiral building block, tartaric acid, protective group, acetal, diisobutylaluminum hydride

JOURNAL FREE ACCESS

1994 Volume 42 Issue 3 Pages 683-685

DOI https://doi.org/10.1248/cpb.42.683

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Abstract

(2S, 3S)-2-(4-Methoxybenzyloxy)-3, 4-O-(3-pentylidene)-1, 3, 4-butanetriol (3), a versatile chiral building block for an essential structural unit of complex natural products, was synthesized starting from dimethyl L-(+)-tartrate (5) on both a small scale and a large scale in good yield.

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