(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one -Drug Synthesis Database

【结构式】

【分子编号】28194

【品名】(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

【CA登记号】

【分子式】C₂₆H₄₂O₇

【分子量】466.61528

【元素组成】C 66.93% H 9.07% O 24%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XII)

Synthesis of intermediate (XII). Ring cleavage and rearrangement of compound (VIII) affords enone (IXa) with an unprotected hydroxyl group. By stereoselective reduction of (IXa), diol (XIa) is obtained, which is finally protected by DHP to obtain intermediate (XII).

参考文献中间体

合成目标

【1】 Jahne, G.; Wess, G.; Bartmann, W.; Beck, G.; Lerch, U.; Liebigs Ann Chem 1987, 321-326.
【2】 Peel, R.; Sutherland, J.K.; Beeley, N.R.A.; Tetrahedron 1981, 37, 411.
【3】 Beck, G.; Dimoxaprost. Drugs Fut 1987, 12, 12, 1101.

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)	13684	3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran	110-87-2	C₅H₈O	详情	详情
(IXa)	28189	(3aR,4R,5R,6aS)-4-[(E)-5-ethoxy-4,4-dimethyl-3-oxo-1-pentenyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one		C₁₆H₂₄O₅	详情	详情
(IXb)	28190	(3aR,4R,5R,6aS)-4-[(E)-5-ethoxy-4,4-dimethyl-3-oxo-1-pentenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₂₉H₃₂O₆	详情	详情
(XIa)	28192	(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-3-hydroxy-4,4-dimethyl-1-pentenyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one		C₁₆H₂₆O₅	详情	详情
(XIb)	28193	(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-3-hydroxy-4,4-dimethyl-1-pentenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₂₉H₃₄O₆	详情	详情
(VIII)	28188	6-chloro-8-[(E)-5-ethoxy-4,4-dimethyl-3-oxo-1-pentenyl]-2-oxabicyclo[3.2.1]octan-3-one		C₁₆H₂₃ClO₄	详情	详情
(X)	28191	2,6-Di-tert-butyl-4-methylphenol diisobutylaluminum salt		C₂₃H₄₁AlO	详情	详情
(XII)	28194	(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one		C₂₆H₄₂O₇	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XII)

Intermediate (XII) is converted in four steps through the «Corey synthesis» to Dimoxaprost.

参考文献中间体

合成目标

【1】 Peel, R.; Sutherland, J.K.; Beeley, N.R.A.; Tetrahedron 1981, 37, 411.
【2】 Jahne, G.; Wess, G.; Bartmann, W.; Beck, G.; Lerch, U.; Liebigs Ann Chem 1987, 321-326.
【3】 Beck, G.; Dimoxaprost. Drugs Fut 1987, 12, 12, 1101.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	28194	(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one		C₂₆H₄₂O₇	详情	详情
(XIII)	28195	(3aR,4R,5R,6aS)-4-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol		C₂₆H₄₄O₇	详情	详情
(XIV)	13616	(4-Carboxybutyl)triphenylphosphonium bromide	17814-85-6	C₂₃H₂₄BrO₂P	详情	详情
(XV)	28196	(Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoic acid		C₃₁H₅₂O₈	详情	详情
(XVI)	28197	(Z)-7-[(1R,2R,3R)-2-[(E,3R)-5-ethoxy-4,4-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]-5-oxo-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoic acid		C₃₁H₅₀O₈	详情	详情

Extended Information