(Z)-7-((1R,2R,3R)-2-[(E,3R)-4,4-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-3-methyl-5-oxocyclopentyl)-5-heptenoic acid -Drug Synthesis Database

【结构式】

【分子编号】37406

【品名】(Z)-7-((1R,2R,3R)-2-[(E,3R)-4,4-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-3-methyl-5-oxocyclopentyl)-5-heptenoic acid

【CA登记号】

【分子式】C₂₉H₄₈O₅

【分子量】476.69712

【元素组成】C 73.07% H 10.15% O 16.78%

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：(XIV)

The Wittig reaction of (XI) with (4-carboxybutyl)triphenylphosphonium bromide (XII) in HMPT gives nat-11R,16,16-trimethyl-15R-(2-tetrahydropyranyloxy)-9S-hydroxyprosta-cis-5-trans-13-dienoic acid (XIII), which is oxidized with Jones reagent (CrO3-H2SO4) affording the corresponding 9-oxo compound (XIV). Finally, this compound is hydrolyzed with acetic acid in a mixture THF-water.

参考文献中间体

合成目标

【1】 Holland, G.W.; et al.; US 4112225 .
【2】 Hillier, K.; Blancafort, P.; Serradell, M.N.; Castaner, J.; RO-21-6937/000. Drugs Fut 1981, 6, 1, 42.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	37403	(3aR,4R,5R,6aS)-4-[(E,3R)-4,4-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-5-methylhexahydro-2H-cyclopenta[b]furan-2-ol		C₂₄H₄₂O₄	详情	详情
(XII)	37404	(3-carboxypropyl)(triphenyl)phosphonium bromide	17857-14-6	C₂₂H₂₂BrO₂P	详情	详情
(XIII)	37405	(Z)-7-((1R,2R,3R,5S)-2-[(E,3R)-4,4-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-5-hydroxy-3-methylcyclopentyl)-5-heptenoic acid		C₂₉H₅₀O₅	详情	详情
(XIV)	37406	(Z)-7-((1R,2R,3R)-2-[(E,3R)-4,4-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-3-methyl-5-oxocyclopentyl)-5-heptenoic acid		C₂₉H₄₈O₅	详情	详情

Extended Information