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【结 构 式】 
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【分子编号】57077 【品名】(2S)-2-[(2R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydro-2-furanyl]-2-hydroxyethyl 3-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C26H29NO7 【 分 子 量 】467.5188 【元素组成】C 66.8% H 6.25% N 3% O 23.96% |
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：(IV)Condensation between N-Boc-nipecotic acid (I) and 2,3-di-O-benzyl ascorbic acid (II) using DCC in the presence of DMAP leads to ester (III). Subsequent removal of the N-Boc group of (III) with trifluoroacetic acid gives the N-deprotected nipecotate (IV). This is finally debenzylated by catalytic hydrogenolysis over Pd/C to furnish the title compound.
| 【1】 Manfredini, S.; Pavan, B.; Vertuani, S.; et al.; Design, synthesis and activity of ascorbic acid prodrugs of nipecotic, kynurenic and diclophenamic acids, liable to increase neurotropic activity. J Med Chem 2002, 45, 3, 559. |
| 【2】 Manfredini, S. (Università di Ferrara); Prodrugs derivs. of the ascorbic acid suitable to the passage of the hematoencephalic barrier. WO 0270499 . |
| 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) | 57078 | Boc-nipecotic acid | C11H19NO4 | 详情 | 详情 | |
| (II) | 57075 | (5R)-3,4-bis(benzyloxy)-5-[(1S)-1,2-dihydroxyethyl]-2(5H)-furanone | C20H20O6 | 详情 | 详情 | |
| (III) | 57076 | 3-{(2S)-2-[(2R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydro-2-furanyl]-2-hydroxyethyl} 1-(tert-butyl) 1,3-piperidinedicarboxylate | C31H37NO9 | 详情 | 详情 | |
| (IV) | 57077 | (2S)-2-[(2R)-3,4-bis(benzyloxy)-5-oxo-2,5-dihydro-2-furanyl]-2-hydroxyethyl 3-piperidinecarboxylate | C26H29NO7 | 详情 | 详情 |
Extended Information