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【结 构 式】 
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【分子编号】53732 【品名】(4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid 【CA登记号】n/a |
【 分 子 式 】C24H38O4 【 分 子 量 】390.56332 【元素组成】C 73.81% H 9.81% O 16.39% |
合成路线1
该中间体在本合成路线中的序号：(XLVIII)Preparation of the key intermediate (XIII) starting from chenodeoxycholic acid (XLIV) was also reported. Diacetylation of (XLIV), followed by selective hydrolysis of diacetate (XLV), gave the C-3 alcohol (XLVI). This was oxidized to dienone (XLVII) following a previously reported procedure. Reduction of (XLVII) by lithium in liquid ammonia yielded the saturated ketone (XLVIII). Protection of the 7-hydroxyl group of (XLVIII) using methoxymethyl chloride, followed by ketalization of the 3-ketone, afforded (XLIX). Side-chain elongation in (XLIX) as in Scheme 20248401a produced (L), which was then deprotected giving (XIII).
| 【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 |
|---|---|---|---|---|---|---|
| (IL) | 53733 | n/a | C28H46O6 | 详情 | 详情 | |
| (VIII) | 53699 | (5S,7R,8R,9S,10S,13R,14S,17R)-17-((1R)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,5-dimethylhexyl)-7-hydroxy-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one | n/a | C33H60O3Si | 详情 | 详情 |
| (XLIV) | 53728 | (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C24H40O4 | 详情 | 详情 |
| (XLV) | 53729 | (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-bis(acetyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C28H44O6 | 详情 | 详情 |
| (XLVI) | 53730 | (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-(acetyloxy)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C26H42O5 | 详情 | 详情 |
| (XLVII) | 53731 | (4R)-4-[(7R,8S,9S,10S,13R,14S,17R)-7-(acetyloxy)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C26H36O5 | 详情 | 详情 |
| (XLVIII) | 53732 | (4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C24H38O4 | 详情 | 详情 |
| (L) | 53734 | n/a | C31H54O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XLVIII)Alternatively, intermediate (XLVIII) can also be obtained by Oppenauer oxidation of chenodeoxycholic acid (XLIV) to yield ketone (LI), which is further oxidized employing SeO2 to provide conjugate ketone (LII). Birch reduction of (LII) with lithium in liquid ammonia led to the trans-fused A-B ring compound (XLVIII).
| 【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 |
|---|---|---|---|---|---|---|
| (XLIV) | 53278 | (2R)-1-[3-(trifluoromethyl)phenoxy]-3-butyn-2-ol | n/a | C11H9F3O2 | 详情 | 详情 |
| (XLVIII) | 53732 | (4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C24H38O4 | 详情 | 详情 |
| (LI) | 53735 | (4R)-4-[(5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C24H38O4 | 详情 | 详情 |
| (LII) | 53736 | (4R)-4-[(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | n/a | C24H36O4 | 详情 | 详情 |