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【结 构 式】 
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【分子编号】11411 【品名】methyl 3-hydroxy-2-[(3-methoxy-3-oxopropyl)sulfanyl]-3-[2-(8-phenyloctyl)phenyl]propanoate 【CA登记号】 |
【 分 子 式 】C28H38O5S 【 分 子 量 】486.67272 【元素组成】C 69.1% H 7.87% O 16.44% S 6.59% |
合成路线1
该中间体在本合成路线中的序号：(V)The synthesis of SK&F 104353 (Ia) was carried out as follows: Darzens condensation of 2-(8-phenyloctyl)benzaldehyde (II) with methyl chloroacetate afforded the trans-epoxide (III), which was opened with methyl mercaptopropionate to give a mixture of regioisomers (IV) and (V). Reaction of this mixture of regioisomers with sodium methoxide produced a mixture of (IV) and starting material (II), which was readily separated by chromatography. Sodium hydroxide saponification of diester (IV) afforded the racemic diacid (I), which was resolved as the alpha-methyl-4-bromobenzylamine salt to give, after conversion to the respective free acids, the enantiomers (Ia) and (Ib).
| 【1】 Gleason, J.G.; Hall, R.F.; Perchonock, C.D.; et al.; High affinity leukotriene receptor antagonists. Synthesis and pharmacological characterization of 2-hydroxy-3-(2-carboxy-ethylthio)-3-[2-(8-phenoyloctyl)propanoic acids. J Med Chem 1987, 30, 6, 959-61. |
| 【2】 Hay, D.W.P.; Newton, J.F.; Torphy, T.J.; Gleason, J.G.; SK&F-104353. Drugs Fut 1990, 15, 3, 240. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11407 | 3-[(2-Carboxyethyl)sulfanyl]-2-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionic acid | C26H34O5S | 详情 | 详情 | |
| (II) | 11408 | 2-(8-Phenyloctyl)benzaldehyde | C21H26O | 详情 | 详情 | |
| (III) | 11409 | methyl 3-[2-(8-phenyloctyl)phenyl]-2-oxiranecarboxylate | C24H30O3 | 详情 | 详情 | |
| (IV) | 11410 | methyl 2-hydroxy-3-[(3-methoxy-3-oxopropyl)sulfanyl]-3-[2-(8-phenyloctyl)phenyl]propanoate | C28H38O5S | 详情 | 详情 | |
| (V) | 11411 | methyl 3-hydroxy-2-[(3-methoxy-3-oxopropyl)sulfanyl]-3-[2-(8-phenyloctyl)phenyl]propanoate | C28H38O5S | 详情 | 详情 |