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【结 构 式】

【分子编号】63559

【品名】methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

【CA登记号】32981-85-4

【 分 子 式 】C17H17NO4

【 分 子 量 】299.32632

【元素组成】C 68.22% H 5.72% N 4.68% O 21.38%

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:(VII)

The asymmetric dihydroxylation of methyl cinnamate (I) with AD-alpha reagent in tert-butanol/water gives the (2R,3S)-dihydroxyester (II), which is treated with trimethyl orthobenzoate (III) and TsOH in dichloromethane yielding the benzoate (IV). This compound, without isolation, is treated with acetyl bromide affording (2S,3R)-2-(benzoyloxy)-3-bromo-3-phenylpropionic acid methyl ester (V), which is treated with sodium azide in DMF to give the corresponding (2R,3S)-azido compound (VI). Finally, this compound is reduced with H2 over Pd/C in methanol to the corresponding amine that suffers a benzoyl transposition yielding the target side chain (VII).

1 Hu, Z.; et al.; Utilization of a benzoyl migration to effect an expeditious synthesis of the paclitaxel C-13 side chain. Org Process Res Dev 1997, 1, 5, 387.
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) 23888 methyl (E)-3-phenyl-2-propenoate 103-26-4 C10H10O2 详情 详情
(II) 38532 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 122743-18-4 C10H12O4 详情 详情
(III) 38531 dimethoxy(phenyl)methyl methyl ether; 1-(trimethoxymethyl)benzene 707-07-3 C10H14O3 详情 详情
(IV) 38533 (1R,2S)-2-hydroxy-1-(methoxycarbonyl)-2-phenylethyl benzoate C17H16O5 详情 详情
(V) 38534 (1S,2R)-2-bromo-1-(methoxycarbonyl)-2-phenylethyl benzoate C17H15BrO4 详情 详情
(VI) 38535 (1R,2S)-2-azido-1-(methoxycarbonyl)-2-phenylethyl benzoate C17H15N3O4 详情 详情
(VII) 63559 methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate 32981-85-4 C17H17NO4 详情 详情
Extended Information