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【结 构 式】 
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【分子编号】50024 【品名】(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-[2-(3-methyl-2-butenyl)-1H-indol-3-yl]propionic acid 【CA登记号】 |
【 分 子 式 】C24H22N2O4 【 分 子 量 】402.44976 【元素组成】C 71.63% H 5.51% N 6.96% O 15.9% |
合成路线1
该中间体在本合成路线中的序号：(I)The esterification of the silylated resin (II) with the prenyltryptophan derivative (I) by means of HATU, OBT and DIEA in DMF gives the resin-bonded ester (III), which is treated with hydrazine in methanol/dichloromethane to eliminate the protecting phthalimido group and yield the resin-bonded tryptophan ester derivative (IV). The condensation of (IV) with N-(Fmoc)-L-proline (V) by means of HATU, HOBT and DIEA in DMF affords the dipeptide (VI), which is treated with piperidine in N-methylpyrrolidine to eliminate the Fmoc protecting group and yield dipeptide ester (VII). Finally, this compound is submitted to an acid-induced cyclization by means of HOAc in refluxing methanol to afford the target bicyclic diketopiperazine.
| 【1】 Wang, B.B.; et al.; Preparation of novel 2-(trialkylsilyl)ethyl linkers and first synthesis of Tryprostatin B on solid phase. Tetrahedron Lett 2001, 42, 8, 1463. |
| 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) | 50024 | (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-[2-(3-methyl-2-butenyl)-1H-indol-3-yl]propionic acid | C24H22N2O4 | 详情 | 详情 | |
| (II) | 50025 | 2-[dimethyl(phenyl)silyl]-1-ethanol | C10H16OSi | 详情 | 详情 | |
| (III) | 50026 | 2-[dimethyl(phenyl)silyl]ethyl (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-[2-(3-methyl-2-butenyl)-1H-indol-3-yl]propanoate | C34H36N2O4Si | 详情 | 详情 | |
| (IV) | 50027 | 2-[dimethyl(phenyl)silyl]ethyl (2S)-2-amino-3-[2-(3-methyl-2-butenyl)-1H-indol-3-yl]propanoate | C26H34N2O2Si | 详情 | 详情 | |
| (V) | 34762 | (2S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-pyrrolidinecarboxylic acid | 71989-31-6 | C20H19NO4 | 详情 | 详情 |
| (VI) | 50028 | 9H-fluoren-9-ylmethyl (2S)-2-[[((1S)-2-[2-[dimethyl(phenyl)silyl]ethoxy]-1-[[2-(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-2-oxoethyl)amino]carbonyl]-1-pyrrolidinecarboxylate | C46H51N3O5Si | 详情 | 详情 | |
| (VII) | 50029 | 2-[dimethyl(phenyl)silyl]ethyl (2S)-3-[2-(3-methyl-2-butenyl)-1H-indol-3-yl]-2-[[(2S)pyrrolidinylcarbonyl]amino]propanoate | C31H41N3O3Si | 详情 | 详情 |