| (R)-(＋)-5-甲基-5-{4-[2-(2-(5-氯吲唑基))乙氧基]苄基}-2,4-噁唑烷二酮的合成及其绝对构型的确定 |
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| 引用本文： | 李雅潇,马慧勇,林紫云,王经斌,杨世颖,张艳红,吕扬,黄海洪.(R)-(＋)-5-甲基-5-{4-[2-(2-(5-氯吲唑基))乙氧基]苄基}-2,4-噁唑烷二酮的合成及其绝对构型的确定[J].有机化学,2009,29(8):1254-1258. |
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| 作者姓名： | 李雅潇 马慧勇 林紫云 王经斌 杨世颖 张艳红 吕扬 黄海洪 |
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| 作者单位： | 1. 中国医学科学院中国协和医科大学药物研究所,北京,100050
2. 国家新药开发工程技术研究中心,北京,102600 |
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| 基金项目： | 国家自然科学基金，北京市自然科学基金 |
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| 摘 要： | 以(S)-(－)-1-苯乙胺为拆分剂对外消旋的α-羟基酸进行拆分, 得到手性α-羟基酯4, 再与尿素合环、脱甲基保护, 得到关键的手性中间体(R)-(＋)-5-甲基-5-(4-羟基苄基)-2,4-噁唑烷二酮(6). 将化合物6与甲磺酸酯(8)缩合即得具有全新化学结构的标题化合物9 (ee值100%), 其结构经1 H NMR和HRMS确证. 根据拆分盐3的单晶X射线衍射分析结果及由α-羟基酯4与尿素合环生成噁唑烷二酮的反应机理, 确定标题化合物9的绝对构型为R.
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| 关 键 词： | 2 4-噁唑烷二酮 化学拆分 单晶X射线衍射 绝对构型 |
| 收稿时间： | 2009-3-17 |
| 修稿时间： | 2009-4-27 |
Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione |
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| Li Yaxiao,Ma Huiyong,Lin Ziyun,Wang Jingbin,Yang Shiying,Zhang Yanhong,L?Yang,Huang Haihong.Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione[J].Chinese Journal of Organic Chemistry,2009,29(8):1254-1258. |
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| Authors: | Li Yaxiao Ma Huiyong Lin Ziyun Wang Jingbin Yang Shiying Zhang Yanhong L?Yang Huang Haihong |
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| Institution: | (a Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050) (b National Engineering Research Center for the Development of New Drugs, Beijing 102600)
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| Abstract: | The chiral α-hydroxyester 4 was obtained by acid catalyzed esterification of the corresponding α-hydroxylacid that was resolved by (S)-(－)-1-phenylethylamine. After cyclization and deprotection, the key intermediate (R)-(＋)-5-methyl-5-(4-hydroxybenzyl)-2,4-oxazolidinedione (6) was obtained. The novel title compound 9 was obtained by the condensation of 6 with methanesulfonate 8. The structure of 9 was confirmed by 1H NMR and HRMS techniques, and its absolute configuration was derived from the X-ray diffraction of R enantiomer of 3. |
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| Keywords: | 2 |
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