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【结 构 式】 
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【分子编号】43186 【品名】(2S,3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol 【CA登记号】 |
【 分 子 式 】C18H24O4 【 分 子 量 】304.38616 【元素组成】C 71.03% H 7.95% O 21.03% |
合成路线1
该中间体在本合成路线中的序号：(VId)The oxidation of protected hydroxymethyl lactone (I) with DCC/DMSO gives the aldehyde (II), which is condensed with phosphorane (III) to yield the pentenone (IV). The reduction of (IV) with NaBH4 in methanol affords the pentenol (Va-b), which is further reduced with DIBAL to provide the lactol (VIa-d). The condensation of (VIa-d) with phosphorane (VII) by means of KOtBu gives the trihydroxyheptenoic acid (VIIIa-b), which is esterified with isopropyl iodide (A) and DBU, yielding the isopropyl ester (IXa-b). Finally, this compound is selectively oxidized with DDQ to afford the target compound.
| 【1】 Stjernschantz, J.; Resul, B.; Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Fut 1992, 17, 8, 691. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IXa) | 19369 | 2-iodopropane | 75-30-9 | C3H7I | 详情 | 详情 |
| (Va) | 43181 | (3aR,4R,5R,6aS)-4-[(E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate | C31H30O5 | 详情 | 详情 | |
| (Vb) | 43182 | (3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate | C31H30O5 | 详情 | 详情 | |
| (VIa) | 43183 | (2R,3aR,4R,5R,6aS)-4-[(E,3R)-3-hydroxy-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol | C18H24O4 | 详情 | 详情 | |
| (VIb) | 43184 | (2S,3aR,4R,5R,6aS)-4-[(E,3R)-3-hydroxy-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol | C18H24O4 | 详情 | 详情 | |
| (VIc) | 43185 | (2R,3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol | C18H24O4 | 详情 | 详情 | |
| (VId) | 43186 | (2S,3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol | C18H24O4 | 详情 | 详情 | |
| (VIIIa) | 43187 | (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoic acid | C23H32O5 | 详情 | 详情 | |
| (VIIIb) | 43188 | (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoic acid | 38344-08-0 | C23H32O5 | 详情 | 详情 |
| (IXb) | 43189 | isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate | C26H38O5 | 详情 | 详情 | |
| (I) | 43178 | (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate | 31752-99-5 | C21H20O5 | 详情 | 详情 |
| (II) | 32042 | (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate | C21H18O5 | 详情 | 详情 | |
| (III) | 43179 | 4-phenyl-1-(triphenylphosphoranylidene)-2-butanone | C28H25OP | 详情 | 详情 | |
| (IV) | 43180 | (3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-5-phenyl-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate | C31H28O5 | 详情 | 详情 | |
| (VII) | 37805 | methyl (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate | C14H17NO3 | 详情 | 详情 | |
| (X) | 43190 | isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate | C26H38O5 | 详情 | 详情 |