【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% |
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 |