• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【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