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【结 构 式】

【分子编号】62441

【品名】 

【CA登记号】

【 分 子 式 】C4H6Cl2O2

【 分 子 量 】156.99584

【元素组成】C 30.6% H 3.85% Cl 45.16% O 20.38%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XVII)

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
Extended Information