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【结 构 式】 
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【分子编号】25480 【品名】tert-butyl (1S,4S,7S)-7-(aminocarbonyl)-15-(9H-fluoren-9-yl)-4-[(1-formyl-1H-indol-3-yl)methyl]-1-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-2,5,13-trioxo-14-oxa-3,6,12-triazapentadec-1-ylcarbamate 【CA登记号】 |
【 分 子 式 】C51H61N9O10S 【 分 子 量 】992.166 【元素组成】C 61.74% H 6.2% N 12.71% O 16.13% S 3.23% |
合成路线1
该中间体在本合成路线中的序号：(VI)The peptide was synthesized by a solid-phase method using a p-methylbenzhydrylamine resin to which N1-Boc-N6-Fmoc-L-lysine (I) was coupled giving (II). To this solid phase the following protected amino acids Nalpha-Boc-N1-formyl-L-tryptophan (III), Nalpha-Boc-Nomega-Tos-L-arginine (V), Nalpha-Boc-D-(2-naphthyl)alanine (VII), Nalpha-Boc-Npi-L-histidine (IX) and Nalpha-Boc-Ogamma-Fm-L-aspartic acid (XI) were sequentially coupled yielding resins (IV), (VI), (VIII), (X) and (XII).
| 【1】 Al-Obeidi, F.A.; Sharma, S.D.; de L. Castrucci, A.; Kesterson, R.A.; Lu, D.; Hadley, M.E.; Cone, R.D.; Hruby, V.J.; Cyclic lactam alpha-melanotropin analogues of Ac-Nle4-cyclo[Asp5, D-Phe7,Lys10] alpha-melanocyte-stimulating hormone-(4-10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem 1995, 38, 18, 3454. |
| 【2】 Hadley, M.E.; Hruby, V.J.; Sharma, S.D. (University of Arizona); Peptides having potent antagonist and agonist bioactivities at melanocortin receptors. US 5731408 . |
| 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) | 25476 | (2S)-2-[(tert-butoxycarbonyl)amino]-6-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid | 84624-27-1 | C26H32N2O6 | 详情 | 详情 |
| (II) | 25477 | 9H-fluoren-9-ylmethyl (5S)-6-amino-5-[(tert-butoxycarbonyl)amino]-6-oxohexylcarbamate | C26H33N3O5 | 详情 | 详情 | |
| (III) | 25478 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1-formyl-1H-indol-3-yl)propionic acid | C17H20N2O5 | 详情 | 详情 | |
| (IV) | 25479 | 9H-fluoren-9-ylmethyl (5S)-6-amino-5-[[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1-formyl-1H-indol-3-yl)propanoyl]amino]-6-oxohexylcarbamate | C38H43N5O7 | 详情 | 详情 | |
| (V) | 19064 | (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]pentanoic acid | C18H28N4O6S | 详情 | 详情 | |
| (VI) | 25480 | tert-butyl (1S,4S,7S)-7-(aminocarbonyl)-15-(9H-fluoren-9-yl)-4-[(1-formyl-1H-indol-3-yl)methyl]-1-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-2,5,13-trioxo-14-oxa-3,6,12-triazapentadec-1-ylcarbamate | C51H61N9O10S | 详情 | 详情 | |
| (VII) | 23498 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionic acid | C18H21NO4 | 详情 | 详情 | |
| (VIII) | 25481 | tert-butyl (1R,4S,7S,10S)-10-(aminocarbonyl)-18-(9H-fluoren-9-yl)-7-[(1-formyl-1H-indol-3-yl)methyl]-4-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-1-(2-naphthylmethyl)-2,5,8,16-tetraoxo-17-oxa-3,6,9,15-tetraazaoctadec-1-ylcarbamate | C64H72N10O11S | 详情 | 详情 | |
| (IX) | 25482 | (2S)-3-[1-[(benzyloxy)methyl]-1H-imidazol-5-yl]-2-[(tert-butoxycarbonyl)amino]propionic acid | 83468-83-1 | C19H25N3O5 | 详情 | 详情 |
| (X) | 25483 | 9H-fluoren-9-ylmethyl (5S,8S,11S,14R,17S)-17-amino-5-(aminocarbonyl)-18-[1-[(benzyloxy)methyl]-1H-imidazol-5-yl]-8-[(1-formyl-1H-indol-3-yl)methyl]-11-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-14-(2-naphthylmethyl)-7,10,13,16-tetraoxo-6,9,12,15-tetraazaoctadec-1-ylcarbamate | C73H79N13O11S | 详情 | 详情 | |
| (XI) | 25484 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]oxy]-4-oxobutyric acid | C24H25NO8 | 详情 | 详情 | |
| (XII) | 25485 | N-(Tert-butoxycarbonyl)-[4-O-(9-fluorenylmethoxycarbonyl)]-L-aspartyl-[N-tau-(benzyloxymethyl)]-D-histidyl-D-2-naphthylalanyl-(N-omega-tosyl)-L-arginyl-(N-1-formyl)-D-tryptophyl-[N-6-(9-fluorenylmethoxycarbonyl)]-L-leucinamide; N-(Tert-butoxycarbonyl)-[4-O-(9-fluorenylmethoxycarbonyl)]-L-aspartyl-[N-tau-(benzyloxymethyl)]-D-histidyl-D-2-naphthylalanyl-(N-omega-tosyl)-L-arginyl-(N-1-formyl)-D-tryptophyl-[N-6-(9-fluorenylmethoxycarbonyl)]-L-leucinamide | C97H102N14O18S | 详情 | 详情 |