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【结 构 式】 
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【分子编号】64553 【品名】Galnon; Fmoc-beta-cyclohexyl-Ala-Lys-AMC 【CA登记号】475115-35-6 |
【 分 子 式 】C40H46N4O6 【 分 子 量 】678.8286 【元素组成】C 70.77% H 6.83% N 8.25% O 14.14% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Coupling of N-alpha-Fmoc-N-epsilon-Boc-lysine (I) to 7-amino-4-methylcoumarin (II) by means of DCC produces the lysine amide (III). After acidic cleavage of the N-Boc protecting group of (III), the resultant primary amine (IV) is attached to chlorotrityl resin to produce (V). The Fmoc group of (V) is then removed with piperidine in DMF, yielding the lysinamide-bound resin (VI). Further coupling with N-Fmoc-cyclohexylalanine (VII) employing TBTU/HOAt furnishes the dipeptide amide resin (VIII). The title compound is finally cleaved from the solid support by means of trifluoroacetic acid in CH2Cl2.
| 【1】 Saar, K.; Mazarati, A.M.; Mahlapuu, R.; Hallnemo, G.; Soomets, U.; Kilk, K.; Hellberg, S.; Pooga, M.; Tolf, B.R.; Shi, T.S.; Hökfelt, T.; Wasterlain, C.; Bartfai, T.; Langel, U.; Anticonvulsant activity of a nonpeptide galanin receptor agonist. Proc Natl Acad Sci USA 2002, 99, 10, 7136. |
| 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) | 18854 | (2S)-6-[(tert-butoxycarbonyl)amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid | C26H32N2O6 | 详情 | 详情 | |
| (II) | 64549 | 7-amino-4-methyl-2H-chromen-2-one | C10H9NO2 | 详情 | 详情 | |
| (III) | 64550 | 9H-fluoren-9-ylmethyl 5-[(tert-butoxycarbonyl)amino]-1-{[(4-methyl-2-oxo-2H-chromen-7-yl)amino]carbonyl}pentylcarbamate | C36H39N3O7 | 详情 | 详情 | |
| (IV) | 64551 | 9H-fluoren-9-ylmethyl 5-amino-1-{[(4-methyl-2-oxo-2H-chromen-7-yl)amino]carbonyl}pentylcarbamate | C31H31N3O5 | 详情 | 详情 | |
| (VI) | 64552 | 2,6-diamino-N-(4-methyl-2-oxo-2H-chromen-7-yl)hexanamide | C16H21N3O3 | 详情 | 详情 | |
| (VII) | 30827 | (2S)-3-cyclohexyl-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C24H27NO4 | 详情 | 详情 | |
| (VIII) | 64553 | Galnon; Fmoc-beta-cyclohexyl-Ala-Lys-AMC | 475115-35-6 | C40H46N4O6 | 详情 | 详情 |