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【结 构 式】 
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【分子编号】54907 【品名】ethyl (4S,5R)-3-benzoyl-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate 【CA登记号】 |
【 分 子 式 】C19H17NO5 【 分 子 量 】339.34772 【元素组成】C 67.25% H 5.05% N 4.13% O 23.57% |
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：(III)The asymmetric dihydroxylation of trans-cinnamic acid ethyl ester (I) with AD mix alpha gives (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid ethyl ester (II), which is submitted to the cyclic iminocarbonate rearrangement protocol with Bu4SnO, PhCO-NCS and MgI2 to yield the chiral oxazolidinone (III). The hydrolysis of (III) in refluxing 10% HCl affords (2R,3S)-3-amino-2-hydroxy-3-phenylpropionic acid (IV), which is finally N-benzoylated by means of benzoyl chloride and NaOH to provide the target side chain acid (V).
| 【1】 Cho, G.Y.; et al.; Improving the regioselectivity in the cyclic iminocarbonate rearrangement: Enantioselective synthesis of the paclitaxel side chain. Bull Korean Chem Soc 2001, 22, 4, 432. |
| 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) | 54905 | Cinnamic acid ethylester; Ethyl cinnamate | C11H12O2 | 详情 | 详情 | |
| (II) | 54906 | ethyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate | C11H14O4 | 详情 | 详情 | |
| (III) | 54907 | ethyl (4S,5R)-3-benzoyl-2-oxo-4-phenyl-1,3-oxazolidine-5-carboxylate | C19H17NO5 | 详情 | 详情 | |
| (IV) | 54908 | (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid | 136561-53-0 | C9H11NO3 | 详情 | 详情 |
| (V) | 31988 | (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropionic acid | C16H15NO4 | 详情 | 详情 |
Extended Information