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【结 构 式】

【分子编号】53709

【品名】(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-[(1R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate

【CA登记号】n/a

【 分 子 式 】C36H67N3O3

【 分 子 量 】589.9464

【元素组成】C 73.29% H 11.45% N 7.12% O 8.14%

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:(XXV)

After protection of triamine (XXIII) as the tris-benzyloxycarbonyl derivative (XXIV), its 7-hydroxyl was acetylated by means of Ac2O and DMAP. Further hydrogenolysis of the benzyloxycarbonyl groups in ethanolic HCl also removed the O-silyl group, yielding (XXV). Treatment of alcohol (XXV) with sulfur trioxide in pyridine generated the pyridinium sulfate salt (XXVI). The 7-acetate ester of (XXVI) was finally hydrolyzed with NaOH to furnish the title compound.

1 Moriarty, R.M.; et al.; Synthesis of squalamine. A steroidal antibiotic from the shark. Tetrahedron Lett 1994, 35, 44, 8103.
2 Moriarty, R.M.; Guo, L.; Tuladhar, S.M. (Genaera Corp.); Chemical synthesis of squalamine. WO 9419366 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXII) 53707 (3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol n/a C40H79N3O2Si 详情 详情
(XXIV) 53708 benzyl 4-{[(benzyloxy)carbonyl]amino}butyl(3-{[(benzyloxy)carbonyl][(3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino}propyl)carbamate n/a C64H97N3O8Si 详情 详情
(XXV) 53709 (3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-[(1R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl acetate n/a C36H67N3O3 详情 详情
(XXVI) 53710 pyridinium (3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(acetyloxy)-3-({3-[(4-aminobutyl)amino]propyl}amino)-17-[(1R)-1,5-dimethyl-4-(sulfonatooxy)hexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene n/a C41H72N4O6S 详情 详情
Extended Information