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【结 构 式】 
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【分子编号】62443 【品名】methyl (3S)-2,2-dichloro-3-hydroxy-3-(4-methoxyphenyl)propanoate 【CA登记号】 |
【 分 子 式 】C11H12Cl2O4 【 分 子 量 】279.11928 【元素组成】C 47.33% H 4.33% Cl 25.4% O 22.93% |
合成路线1
该中间体在本合成路线中的序号：(XIX)A new enantioselective method for the preparation of glycidic ester (XIV) has been disclosed. Methyl trichloroacetate (XVI) was converted to the dichloroketene silyl acetal (XVII) by treatment with zinc powder and chlorotrimethylsilane. Asymmetric aldol condensation of (XVII) with anisaldehyde (X) in the presence of the chiral oxazaborolidine catalyst (XVIII) at -78 C produced methyl (S)-2,2-dichloro-3-hydroxy-3-(4-methoxyphenyl)propionate (XIX). Reductive mono-dechlorination of (XIX) furnished chlorohydrin (XX), which was then cyclized to glycidic ester (XIV) in the presence of NaOMe
| 【1】 Imashiro, R.; Kuroda, T.; Asymmetric synthesis of methyl (2R,3S)-3-(4-methoxyphenyl) glycidate, a key intermediate of diltiazem, via Mukaiyama aldol reaction. Tetrahedron Lett 2001, 42, 7, 1313. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 27251 | 4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde | 123-11-5 | C8H8O2 | 详情 | 详情 |
| (XIV) | 62435 | ethyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate | C12H14O4 | 详情 | 详情 | |
| (XVI) | 62440 | methyl 2,2,2-trichloroacetate | 598-99-2 | C3H3Cl3O2 | 详情 | 详情 |
| (XVII) | 62441 | C4H6Cl2O2 | 详情 | 详情 | ||
| (XVIII) | 62442 | C6H12BNO2 | 详情 | 详情 | ||
| (XIX) | 62443 | methyl (3S)-2,2-dichloro-3-hydroxy-3-(4-methoxyphenyl)propanoate | C11H12Cl2O4 | 详情 | 详情 | |
| (XX) | 62444 | methyl (3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propanoate | C11H13ClO4 | 详情 | 详情 |