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【结 构 式】 
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【分子编号】20990 【品名】methyl (Z)-7-[(1R,2S,3R,5R)-5-(formyloxy)-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate 【CA登记号】 |
【 分 子 式 】C38H62O8 【 分 子 量 】646.90548 【元素组成】C 70.55% H 9.66% O 19.79% |
合成路线1
该中间体在本合成路线中的序号：(XX)The protection of (XVI) with dihydropyran as usual gives the fully protected compound (XVII), which is deacetylated with K2CO3 in methanol to the 9alpha-hydroxy derivative (XVIII). The formylation of (XVIII) with diethyl azodiformate (XIX) and triphenylphosphine - formic acid in THF gives the 9beta-formyloxy compound (XX), which is hydrolyzed with K2CO3 as before to the 9beta-hydroxy compound (XXI). The tosylation of (XXI) with tosyl chloride in pyridine yields the tosylate (XXII), which is deprotected with p-toluenesulfonic acid affording the 9beta-tosyloxy-11alpha,15alpha-dihydroxyprostaglandin (XXIII). Finally, this compound is cyclized with sodium azide in hot DMSO.
| 【1】 Masuda, Y. (Ono Pharmaceutical Co., Ltd.); New method of treatment using prostaglandin analogues. EP 0169725; JP 1986030519 . |
| 【2】 Prous, J.; Castaner, J.; OP-2507. Drugs Fut 1989, 14, 6, 525. |
| 【3】 Iguchi, S.; et al.; T. Synthesis of 15-cis-(4-n-propylcyclohexyl)-16,17,18,19, 20-pentanor-9-deoxy-6,9-alpha-nitriloprostaglandin F2 methyl ester (OP-2507), a novel anti-cerebral ischemic agent. Chem Pharm Bull 1988, 36, 3, 1128. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 20985 | methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-[(E,3S)-3-hydroxy-3-(4-propylcyclohexyl)-1-propenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C33H54O7 | 详情 | 详情 | |
| (XVII) | 20987 | methyl (Z)-7-[(1R,2S,3R,5S)-5-(acetoxy)-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C39H64O8 | 详情 | 详情 | |
| (XVIII) | 20988 | methyl (Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C37H62O7 | 详情 | 详情 | |
| (XIX) | 20989 | Diethylazadicarboxylate; Diethyl Azodiformate; Azodiformic Acid Diethyl Ester; Diethyl Azodicarboxylate; Azodicarboxylic Acid Diethyl Ester; Diethyl 1,2-diazenedicarboxylate | 1972-28-7 | C6H10N2O4 | 详情 | 详情 |
| (XX) | 20990 | methyl (Z)-7-[(1R,2S,3R,5R)-5-(formyloxy)-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C38H62O8 | 详情 | 详情 | |
| (XXI) | 20991 | methyl (Z)-7-[(1R,2S,3R,5R)-5-hydroxy-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C37H62O7 | 详情 | 详情 | |
| (XXII) | 20992 | methyl (Z)-7-[(1R,2S,3R,5R)-5-[[(4-methylphenyl)sulfonyl]oxy]-2-[(E,3S)-3-(4-propylcyclohexyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate | C44H68O9S | 详情 | 详情 | |
| (XXIII) | 20993 | methyl (Z)-7-((1R,2R,3R,5R)-3-hydroxy-2-[(E,3S)-3-hydroxy-3-(4-propylcyclohexyl)-1-propenyl]-5-[[(4-methylphenyl)sulfonyl]oxy]cyclopentyl)-5-heptenoate | C32H48O7S | 详情 | 详情 |