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【结 构 式】 
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【分子编号】34347 【品名】ethyl (3aS,4S,5R,6aR)-2-(1-hydroxy-5-methoxy-5-oxopentyl)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]octahydro-2-pentalenecarboxylate 【CA登记号】 |
【 分 子 式 】C37H62O9 【 分 子 量 】650.89388 【元素组成】C 68.28% H 9.6% O 22.12% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The protection of (XI) with dihydropyran as usual affords the bistetrahydropyranylether (XII), which is deacetylated with K2CO3 in methanol to the 5-hydroxyester (XIII). Total hydrolysis of (XIII) with aqueous KOH gives the diacid (XIV), which is submitted to a dehydrative decarboxylation with N,N-dimethylformamide dimethyl acetal (A) in CHCl3 yielding the protected carbacyclin (XV). Finally, this compound is deprotected with aqueous acetic acid and hydrolyzed with KOH.
| 【1】 Sakai, K.; Amemiya, S.; Kojima, K.; A novel synthesis (±)-carbacyclin. Chem Pharm Bull 1984, 32, 4, 1349-54. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (XI) | 34345 | ethyl (3aS,4S,5R,6aR)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-4-[(E,3S)-3-hydroxy-1-octenyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]octahydro-2-pentalenecarboxylate | C33H54O9 | 详情 | 详情 | |
| (XII) | 34346 | ethyl (3aS,4S,5R,6aR)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]octahydro-2-pentalenecarboxylate | C39H64O10 | 详情 | 详情 | |
| (XIII) | 34347 | ethyl (3aS,4S,5R,6aR)-2-(1-hydroxy-5-methoxy-5-oxopentyl)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]octahydro-2-pentalenecarboxylate | C37H62O9 | 详情 | 详情 | |
| (XIV) | 34348 | (3aS,4S,5R,6aR)-2-(4-carboxy-1-hydroxybutyl)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]octahydro-2-pentalenecarboxylic acid | C34H56O9 | 详情 | 详情 | |
| (XV) | 34349 | methyl 5-[(3aS,4S,5R,6aR)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoate | C34H56O6 | 详情 | 详情 |