- Optically Active trans-Diethylstilbesterol Oxide Monomethyl Ether
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Diethylstilbestrol oxide is a metabolic intermediate of diethylstilbestrol.In order to elucidate the effects of optically active diethylstilbestrol oxides on microtubule assembly and cell culture, we synthesized (+/-)-diethylstilbestrol oxide (2a).Since 2a was not stable under moderately acidic and basic conditions, the monomethyl ether (2c) of diethylstilbestrol oxide, which was more stable than 2a, was separated by high-pressure liquid chromatography using a chiral column.The mono (4-bromobenzoate) of (-)-2c was analyzed by X-ray crystallography and its absolute structure was determined as C (1R,1'R).Keywords: optical resolution; diethylstilbestrol oxide monomethyl ether; absolute structure; X-ray crystallography; pig liver esterase; diethylstilbestrol oxide
- Oda, Taiko,Watanuki, Mitsuru,Sato, Yoshihiro,Hata, Tadashi
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p. 810 - 815
(2007/10/02)
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