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【结 构 式】 
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【分子编号】27447 【品名】(2S)-2-([[(3S,6S,9S,12S)-6-benzyl-12-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetoxy)methyl]tetrahydro-2H-pyran-2-yl]sulfanyl)propanoyl]amino]-9-(1H-indol-3-ylmethyl)-5,8,11,14-tetraoxo-1,4,7,10-tetraazacyclotetradecan-3-yl]carbonyl]amino)-4-methylpentanoic acid 【CA登记号】 |
【 分 子 式 】C55H72N8O19S 【 分 子 量 】1181.2852 【元素组成】C 55.92% H 6.14% N 9.49% O 25.73% S 2.71% |
合成路线1
该中间体在本合成路线中的序号：(XII)The deprotection of the Boc-amino group of the aspartic acid of (X) allows its condensation with the protected S-(tetra-O-acetyl-beta-D-galactopyranosyl)-L-cysteine (XI) affording the monocyclic hexapeptide (XII), which is treated first with HF, SMe2, p-cresol, and p-thiocresol to eliminate the solid phase resin and the Boc protecting group of the cysteine residue, and then cyclized by means of PyBop to afford the bicyclic hexapeptide (XIII). Finally, this compound is treated with sodium methoxide (c>5 mM) for more than 5 h. to give a mixture of the already known galactopyranosyl-hexapaptide Neuronorm (XIV) and the target compound (the dehydroalanyl derivative), which were separated by RP-HPLC.
| 【1】 Lombardi, A.; D'Agostino, B.; Nastri, F.; D'Andrea, L.D.; Filippelli, A.; Rossi, F.; Pavone, V.; A novel super-potent neurokinin A receptor antagonist containing dehydroalanine. Bioorg Med Chem Lett 1998, 8, 10, 1153. |
| 【2】 Lombardi, A.; D'Agostino, B.; Filippelli, A.; Pedone, C.; Matera, M.G.; Falciani, M.; De Rosa, M.; Rossi, F.; Pavone, V.; Neuronorm is a potent and water soluble neurokinin A receptor antagonist. Bioorg Med Chem Lett 1998, 8, 13, 1735. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 27445 | (2S)-2-([[(3S,6S,9S,12S)-6-benzyl-12-[(tert-butoxycarbonyl)amino]-9-(1H-indol-3-ylmethyl)-5,8,11,14-tetraoxo-1,4,7,10-tetraazacyclotetradecan-3-yl]carbonyl]amino)-4-methylpentanoic acid | C38H49N7O9 | 详情 | 详情 | |
| (XI) | 27446 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetoxy)methyl]tetrahydro-2H-pyran-2-yl]sulfanyl)propionic acid | C22H33NO13S | 详情 | 详情 | |
| (XII) | 27447 | (2S)-2-([[(3S,6S,9S,12S)-6-benzyl-12-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetoxy)methyl]tetrahydro-2H-pyran-2-yl]sulfanyl)propanoyl]amino]-9-(1H-indol-3-ylmethyl)-5,8,11,14-tetraoxo-1,4,7,10-tetraazacyclotetradecan-3-yl]carbonyl]amino)-4-methylpentanoic acid | C55H72N8O19S | 详情 | 详情 | |
| (XIII) | 27448 | (2R,3R,4S,5R,6S)-3,5-bis(acetoxy)-2-[(acetoxy)methyl]-6-([[(1S,4S,7S,10S,13R,16S)-4-benzyl-7-(1H-indol-3-ylmethyl)-16-isobutyl-3,6,9,12,15,18,21-heptaoxo-2,5,8,11,14,17,20-heptaazabicyclo[8.8.4]docos-13-yl]methyl]sulfanyl)tetrahydro-2H-pyran-4-yl acetate | C50H62N8O16S | 详情 | 详情 | |
| (XIV) | 27449 | (1S,4S,7S,10S,13R,16S)-4-benzyl-7-(1H-indol-3-ylmethyl)-16-isobutyl-13-([[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]sulfanyl]methyl)-2,5,8,11,14,17,20-heptaazabicyclo[8.8.4]docosane-3,6,9,12,15,18,21-heptone | C42H54N8O12S | 详情 | 详情 |