|
【结 构 式】 
|
【分子编号】53721 【品名】({(4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl}oxy)(tert-butyl)dimethylsilane; benzyl (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl ether 【CA登记号】n/a |
【 分 子 式 】C45H76O4Si 【 分 子 量 】709.18154 【元素组成】C 76.21% H 10.8% O 9.02% Si 3.96% |
合成路线1
该中间体在本合成路线中的序号：(XXXVII)After silylation of alcohol (XXXVI) to silyl ether (XXXVII), its tetrahydropyranyl protecting group was selectively removed by treatment with magnesium bromide in Et2O. The resultant 3-beta alcohol (XXXVIII) was oxidized to ketone (XXXIX) employing Collin's reagent. The polyamino side-chain was then introduced in (XXXIX) by reductive amination with the di-Boc-protected spermidine (XL) in the presence of NaBH3CN, giving (XLI) as a mixture of 3-alpha and 3-beta isomers.
| 【1】 Pechulis, A.D.; et al.; Synthesis of 24xi-squalamine, an anti-infective steroidal polyamine. J Org Chem 1995, 60, 16, 5121. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXVI) | 53720 | (6R)-6-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-heptanol | n/a | C39H62O4 | 详情 | 详情 |
| (XXXVII) | 53721 | ({(4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl}oxy)(tert-butyl)dimethylsilane; benzyl (3S,5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl ether | n/a | C45H76O4Si | 详情 | 详情 |
| (XXXVIII) | 53722 | (3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | n/a | C40H68O3Si | 详情 | 详情 |
| (XXXIX) | 53723 | (5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one | n/a | C40H66O3Si | 详情 | 详情 |
| (XL) | 53724 | tert-butyl 3-aminopropyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C17H35N3O4 | 详情 | 详情 |
| (XLI) | 53725 | tert-butyl 3-{[(5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino}propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C57H101N3O6Si | 详情 | 详情 |