标题:Facile Synthesis of Enantiomerically Pure 1-(5-Bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane
作者:Zhang Shuo; Wang Wenjin; Li Chuan; Liu Peng; Xu Weiren; Tang Lida; Wang Jianwu; Zhao Guilong
作者机构:[Zhang, S] School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China, Tianjin Key Laboratory of Molecular Design and Dru 更多
通讯作者:Wang, J(jwwang@sdu.edu.cn)
通讯作者地址:[Wang, JW]Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China.
来源:高等学校化学研究(英文版)
出版年:2014
卷:30
期:2
页码:250-256
DOI:10.1007/s40242-014-3257-1
关键词:Diarylethane;Diastereomer;Enantiomer;Resolution;SGLT2 inhibitor
摘要:A facile 7-step procedure for the synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4ethoxyphenyl)ethanes[(R)-2 and(S)-2] that started from (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone 3 was developed. The key step was the resolution of 2-(5-bromo-2-chlorophenyl)-2-(4-ethoxyphenyl)acetic acid 6 by crystallizations of its L- and D-menthyl esters 7 and 8 from petroleum ether to give optically pure enantiomers 9 and 10, respectively. The absolute configurations of the products were unambiguously determined by single-crystal X-ray diffractions of four key intermediates, 9, 10, 13 and 14. This procedure is characterized by inexpensiveness, scalability and ability to produce two individual enantiomers of a diarylethane with unambiguously determined absolute configurations and high enantiomeric purities.
收录类别:CSCD;SCOPUS;SCIE
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84897951358&doi=10.1007%2fs40242-014-3257-1&partnerID=40&md5=f00759f42bbbce673b83590b49529d2a
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