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【结 构 式】 
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【分子编号】61394 【品名】(2S)-1-{(2S)-2-{[(2S,3S)-2-amino-3-methylpentanoyl]amino}-5-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]pentanoyl}-2-pyrrolidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C31H52N6O7S 【 分 子 量 】652.85612 【元素组成】C 57.03% H 8.03% N 12.87% O 17.15% S 4.91% |
合成路线1
该中间体在本合成路线中的序号：(VI)The title compound is prepared by solid-phase peptide synthesis using an automatic peptide synthesizer. To the L-proline attached to the resin support (I) is coupled Fmoc-L-Arg(Pmc)-OH (II) under activation with HBTU/HOBt to produce the protected dipeptide resin (III). The N-Fmoc group of (III) is then removed by means of piperidine in DMF, yielding the deprotected amine (IV). Subsequent coupling with N-Fmoc-L-isoleucine (V), followed by deprotection with piperidine in DMF, leads to the tripeptide resin (VI). Further coupling/deprotection cycles with N-Fmoc-L-norvaline (VII) and N-Fmoc-O-t-butyl-L-threonine (IX) produce resins (VIII) and (X) respectively.
| 【1】 Haviv, F.; Kalvin, D.M.; Henkin, J.; Bradley, M.F.; Schneider, A.J. (Abbott Laboratories Inc.); Peptide antiangiogenic drugs. JP 2002516342; WO 9961476 . |
| 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) | 16731 | L-proline | 147-85-3 | C5H9NO2 | 详情 | 详情 |
| (II) | 49886 | (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoic acid | C35H44N4O7S | 详情 | 详情 | |
| (III) | 61391 | (2S)-1-{(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]pentanoyl}-2-pyrrolidinecarboxylic acid | C40H51N5O8S | 详情 | 详情 | |
| (IV) | 61392 | (2S)-1-{(2S)-2-amino-5-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]pentanoyl}-2-pyrrolidinecarboxylic acid | C25H41N5O6S | 详情 | 详情 | |
| (V) | 61393 | (2S,3S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-methylpentanoic acid | C21H23NO4 | 详情 | 详情 | |
| (VI) | 61394 | (2S)-1-{(2S)-2-{[(2S,3S)-2-amino-3-methylpentanoyl]amino}-5-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]pentanoyl}-2-pyrrolidinecarboxylic acid | C31H52N6O7S | 详情 | 详情 | |
| (VII) | 61395 | (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pentanoic acid | C20H21NO4 | 详情 | 详情 | |
| (VIII) | 61396 | (2S)-1-{(2S)-2-[((2S,3S)-2-{[(2S)-2-aminopentanoyl]amino}-3-methylpentanoyl)amino]-5-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]pentanoyl}-2-pyrrolidinecarboxylic acid | C36H61N7O8S | 详情 | 详情 | |
| (IX) | 61397 | tert-butyl (2S,3R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxybutanoate | C23H27NO5 | 详情 | 详情 | |
| (X) | 61398 | (2S)-1-{(2S,5S,8S,11S,12R)-11-amino-2-{3-[(imino{[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino}methyl)amino]propyl}-12,14,14-trimethyl-5-[(1S)-1-methylpropyl]-4,7,10-trioxo-8-propyl-13-oxa-3,6,9-triazapentadec-1-anoyl}-2-pyrrolidinecarboxylic acid | C44H76N8O10S | 详情 | 详情 |