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【结 构 式】 
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【分子编号】32399 【品名】4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-[(tert-butoxycarbonyl)amino]butanedioate 【CA登记号】 |
【 分 子 式 】C25H31NO8S 【 分 子 量 】505.58908 【元素组成】C 59.39% H 6.18% N 2.77% O 25.32% S 6.34% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The esterification of N-(benzyloxycarbonyl)-L-aspartic acid 4-O-benzyl monoester (VII) with 2-(p-toluenesulfonyl)ethanol by means of DCC and pyridine gives the mixed diester (VIII), which is deprotected at the amino group with HCl in dioxane yielding compound (IX). The condensation of (IX) with protected glutamic acid (X) by means of HOBt, DIEA and WSC carbodiimide affords dipeptide (XI), which is deprotected with HCl as before giving (XII). The condensation of (XII) with pyroglutamic acid (XIII) as before yields tripeptide (XIV), which is deprotected at the terminal carboxy group by means of diazabicyclo[4.3.0]non-5-ene (DBN) providing tripeptide (XV).
| 【1】 Hiebl, J.; et al.; Large-scale synthesis of hematoregulatory nonapeptide SK&F 107647 by fragment coupling. J Pept Res 1999, 54, 1, 54. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40676 | 2-[(4-Methylphenyl)sulfonyl]ethanol; 2-[(4-methylphenyl)sulfonyl]-1-ethanol | 22381-54-0 | C9H12O3S | 详情 | 详情 | |
| (VII) | 25219 | (2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutyric acid | 7536-58-5 | C16H21NO6 | 详情 | 详情 |
| (VIII) | 32399 | 4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-[(tert-butoxycarbonyl)amino]butanedioate | C25H31NO8S | 详情 | 详情 | |
| (IX) | 32400 | 4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-aminobutanedioate | C20H23NO6S | 详情 | 详情 | |
| (X) | 25141 | (2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid | 13574-13-5 | C17H23NO6 | 详情 | 详情 |
| (XI) | 32401 | 4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-([(2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoyl]amino)butanedioate | C37H44N2O11S | 详情 | 详情 | |
| (XII) | 32402 | 4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-[[(2S)-2-amino-5-(benzyloxy)-5-oxopentanoyl]amino]butanedioate | C32H36N2O9S | 详情 | 详情 | |
| (XIII) | 32406 | (2S)-5-oxo-2-pyrrolidinecarboxylic acid | 98-79-3 | C5H7NO3 | 详情 | 详情 |
| (XIV) | 32403 | 4-benzyl 1-[2-[(4-methylphenyl)sulfonyl]ethyl] (2S)-2-[[(2S)-5-(benzyloxy)-5-oxo-2-([[(2S)-5-oxopyrrolidinyl]carbonyl]amino)pentanoyl]amino]butanedioate | C37H41N3O11S | 详情 | 详情 | |
| (XV) | 32404 | (2S)-4-(benzyloxy)-2-[[(2S)-5-(benzyloxy)-5-oxo-2-([[(2S)-5-oxopyrrolidinyl]carbonyl]amino)pentanoyl]amino]-4-oxobutyric acid | C28H31N3O9 | 详情 | 详情 |