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【结 构 式】 
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【分子编号】50813 【品名】methyl (2S)-1-[(2S)-2-(benzyloxy)propanoyl]-2-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C16H21NO4 【 分 子 量 】291.34708 【元素组成】C 65.96% H 7.27% N 4.81% O 21.97% |
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：(XIX)Removal of the Z protecting group of (XIV) by hydrogenation over Pd/C gives secondary amine (XV), which is then condensed with carboxylic acid derivative (XVI) by means of EDC to furnish benzyl-protected didemnin B (XX) (in turn, synthesis of (XVI) can be performed by coupling of O-benzyl lactyl azide (obtained from ethyl O-benzyl lactate (XVII)) with Pro-OMe (XVIII) to afford methyl ester (XIX), followed by saponification of the methyl ester with NaOH). Finally, didemnin B is obtained by hydrogenation of (XX) over Pd/C for benzyl group removal.
| 【1】 Rinehart, K.L.; et al.; Total synthesis of didemnins A, B, and C. J Am Chem Soc 1987, 109, 22, 6846. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 50810 | benzyl (1R)-1-[([(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin | C57H84N6O14 | 详情 | 详情 | |
| (XV) | 50796 | (2R)-N-[(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]-4-methyl-2-(methylamino)pentanamide | C49H78N6O12 | 详情 | 详情 | |
| (XVI) | 50798 | (2S)-1-[(2S)-2-(benzyloxy)propanoyl]-2-pyrrolidinecarboxylic acid | C15H19NO4 | 详情 | 详情 | |
| (XVII) | 50812 | ethyl (2S)-2-(benzyloxy)propanoate | C12H16O3 | 详情 | 详情 | |
| (XVIII) | 29552 | methyl (2S)-2-pyrrolidinecarboxylate | 2133-40-6 | C6H11NO2 | 详情 | 详情 |
| (XIX) | 50813 | methyl (2S)-1-[(2S)-2-(benzyloxy)propanoyl]-2-pyrrolidinecarboxylate | C16H21NO4 | 详情 | 详情 | |
| (XX) | 50811 | (2S)-N-[(1R)-1-[([(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-10-[(1S)-1-methylpropyl]-1,4,8,13,16,18,21-heptaoxodocosahydro-15H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl]amino)carbonyl]-3-methylbutyl]-1-[(2S)-2-(benzyloxy)propanoyl]-N-methyl-2-pyrrolidinecarboxamide | C64H95N7O15 | 详情 | 详情 |
Extended Information