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【结 构 式】

【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%

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:(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
Extended Information