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 -Drug Synthesis Database

【结构式】

【分子编号】20993

【品名】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

【CA登记号】

【分子式】C₃₂H₄₈O₇S

【分子量】576.79492

【元素组成】C 66.64% H 8.39% O 19.42% S 5.56%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XXIII)

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.

参考文献中间体

合成目标

【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

Extended Information