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【结 构 式】 
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【分子编号】53746 【品名】tert-butyl 3-({(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl}amino)propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate 【CA登记号】n/a |
【 分 子 式 】C51H87N3O6 【 分 子 量 】838.2684 【元素组成】C 73.07% H 10.46% N 5.01% O 11.45% |
合成路线1
该中间体在本合成路线中的序号：(LXIII)Optionally, acetate ester hydrolysis of intermediate (LVIII), followed by regioselective alcohol oxidation with Collin's reagent, yielded ketone (LX). The 7-hydroxyl group of (LX) was then protected by benzylation to afford (LXI). Reductive amination of ketone (LXI) with the di-Boc-protected spermidine (XL) provided the polyamino sterol (LXII). After hydrolysis of the ethylidene ketal group of (LXII), the resultant ketone was reduced by NaBH4 to give alcohol (LXIII).
| 【1】 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 |
|---|---|---|---|---|---|---|
| (XL) | 53724 | tert-butyl 3-aminopropyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C17H35N3O4 | 详情 | 详情 |
| (LVIII) | 53741 | (3S,5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | n/a | C31H52O5 | 详情 | 详情 |
| (LX) | 53743 | (5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one | n/a | C29H48O4 | 详情 | 详情 |
| (LXI) | 53744 | (5S,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one | n/a | C36H54O4 | 详情 | 详情 |
| (LXII) | 53745 | tert-butyl 3-({(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-3-(2-isopropyl-1,3-dioxolan-2-yl)-1-methylpropyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl}amino)propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C53H89N3O7 | 详情 | 详情 |
| (LXIII) | 53746 | tert-butyl 3-({(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl}amino)propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C51H87N3O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(LXIII)Sulfation of alcohol (LXIII) with SO3-pyridine yielded (LXIV). After acidic Boc group cleavage, the resultant compound (LXV) was subjected to benzyl group hydrogenolysis to give the title compound.
| 【1】 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 |
|---|---|---|---|---|---|---|
| (LXIII) | 53746 | tert-butyl 3-({(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl}amino)propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C51H87N3O6 | 详情 | 详情 |
| (LXIV) | 53747 | tert-butyl 3-({(3S,5R,7R,8R,9S,10S,13R,14S,17R)-7-(benzyloxy)-17-[(1R)-1,5-dimethyl-4-(sulfooxy)hexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl}amino)propyl{4-[(tert-butoxycarbonyl)amino]butyl}carbamate | n/a | C51H87N3O9S | 详情 | 详情 |
| (LXV) | 53748 | (4R)-4-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(4-aminobutyl)amino]propyl}amino)-7-(benzyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate | n/a | C41H71N3O5S | 详情 | 详情 |