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【结 构 式】

【分子编号】27449

【品名】(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

【CA登记号】

【 分 子 式 】C42H54N8O12S

【 分 子 量 】895.00348

【元素组成】C 56.36% H 6.08% N 12.52% O 21.45% S 3.58%

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:(XIV)

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
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