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【结 构 式】 
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【分子编号】34340 【品名】ethyl (3R,4S)-1-[1-(acetoxy)-5-methoxy-5-oxopentyl]-3,4-bis(2-oxoethyl)cyclopentanecarboxylate 【CA登记号】 |
【 分 子 式 】C20H30O8 【 分 子 量 】398.4534 【元素组成】C 60.29% H 7.59% O 32.12% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of ethyl bicyclo[4.3.0]nona-3-ene-8-carboxylate (I) with methyl 4-chloroformylbutanoate (II) by means of lithium diisopropylamide in THF yields the ketodiester (III), which is reduced with NaBH4 in methanol to the hydroxydiester (IV). Acetylation of (IV) in the usual way affords the acetate (V), which is submitted to ozonolysis with O3 to give the dialdehyde (VI). The intramolecular aldol condensation of (VI) by means of Zn++ yields the desired hydroxyaldehyde (VII), which is submitted to a Horner-Wittig condensation with 2-oxoheptylidenetributylphosphorane (VIII) affording the enone (IX). The protection of the enone (X) with dihydropyran as usual yields the tetrahydropyranylether (X), which is reduced with NaSH4 in methanol to the unsaturated alcohol (Xl).
| 【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 |
|---|---|---|---|---|---|---|
| (I) | 34336 | ethyl (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate | C12H18O2 | 详情 | 详情 | |
| (II) | 20650 | methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate | 1501-26-4 | C6H9ClO3 | 详情 | 详情 |
| (III) | 34337 | ethyl (3aR,7aS)-2-(5-methoxy-5-oxopentanoyl)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate | C18H26O5 | 详情 | 详情 | |
| (IV) | 34338 | ethyl (3aR,7aS)-2-(1-hydroxy-5-methoxy-5-oxopentyl)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate | C18H28O5 | 详情 | 详情 | |
| (V) | 34339 | ethyl (3aR,7aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate | C20H30O6 | 详情 | 详情 | |
| (VI) | 34340 | ethyl (3R,4S)-1-[1-(acetoxy)-5-methoxy-5-oxopentyl]-3,4-bis(2-oxoethyl)cyclopentanecarboxylate | C20H30O8 | 详情 | 详情 | |
| (VII) | 34341 | ethyl (3aS,4R,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-4-formyl-5-hydroxyoctahydro-2-pentalenecarboxylate | C20H30O8 | 详情 | 详情 | |
| (VIII) | 34342 | 1-(tributylphosphoranylidene)-2-heptanone | C19H39OP | 详情 | 详情 | |
| (IX) | 34343 | ethyl (3aS,4S,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-5-hydroxy-4-[(E)-3-oxo-1-octenyl]octahydro-2-pentalenecarboxylate | C27H42O8 | 详情 | 详情 | |
| (X) | 34344 | ethyl (3aS,4S,5R,6aR)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-4-[(E)-3-oxo-1-octenyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]octahydro-2-pentalenecarboxylate | C33H52O9 | 详情 | 详情 |