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【结 构 式】

【分子编号】13613

【品名】(3aR,4R,5R,6aS)-4-[2-(2-heptyl-1,3-dioxolan-2-yl)ethyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

【CA登记号】

【 分 子 式 】C32H40O6

【 分 子 量 】520.666

【元素组成】C 73.82% H 7.74% O 18.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

The condensation of dimethyl methylphosphonate (I) with ethyl octanoate (II) by means of butyllithium in THF gives dimethyl 2-oxononylphosphonate (III), which is condensed with the protected aldehyde (IV) by means of NaH in THF, yielding the unsaturated ketone (V). The hydrogenation of (V) with H2 over Pd/C in ethyl acetate affords the corresponding saturated ketone (VI), which is treated with ethylene glycol and p-toluenesulfonic acid to give the cyclic ketal (VII). The mild hydrolysis of (VII) with K2CO3 and acetic acid gives the alcohol derivative (VIII); the reduction of the lactone group of (VIII) with dibutylaluminum hydride in toluene affords the lactol (IX), which is condensed with (4-carboxybutyl)triphenylphosphonium bromide (X) by means of NaH in DMSO yielding the protected prostaglandin (XI). Esterification of (XI) with isopropyl iodide and DBU in acetonitrile gives the precursor (XII), which is finally deprotected with acetic acid in THF - water.

1 Ueno, R.; Ueno, R.; Oda, T. (Ueno Fine Chemicals Industry, Ltd.); Prostaglandins of the F series. EP 0289349; JP 1989151552; US 5001153; US 5106869 .
2 Ueno, R.; Ueno, R.; Oda, T. (Ueno Fine Chemicals Industry, Ltd.); 13,14-Dihydro-15-keto-PGFs. GB 2225573 .
3 Ueno, R.; Ueno, R.; Oda, T. (Ueno Fine Chemicals Industry, Ltd.); Ocular hypotensive agents. EP 0308135; JP 1994080571; US 5151444; US 5166178; US 5212200 .
4 Prous, J.; Castaner, J.; UF-021. Drugs Fut 1992, 17, 3, 193.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13607 dimethyl methylphosphonate 756-79-6 C3H9O3P 详情 详情
(II) 13608 ethyl octanoate; ethyl caprylate 106-32-1 C10H20O2 详情 详情
(III) 13609 dimethyl 2-oxononylphosphonate C11H23O4P 详情 详情
(IV) 13610 (3aR,4R,5R,6aS)-2-oxo-4-(2-oxoethyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C22H20O5 详情 详情
(V) 13611 (3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-1-decenyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C30H34O5 详情 详情
(VI) 13612 (3aR,4R,5R,6aS)-2-oxo-4-(3-oxodecyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C30H36O5 详情 详情
(VII) 13613 (3aR,4R,5R,6aS)-4-[2-(2-heptyl-1,3-dioxolan-2-yl)ethyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C32H40O6 详情 详情
(VIII) 13614 (3aR,4R,5R,6aS)-4-[2-(2-Heptyl-1,3-dioxolan-2-yl)ethyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one C19H32O5 详情 详情
(IX) 13615 (3aR,4R,5R,6aS)-4-[2-(2-Heptyl-1,3-dioxolan-2-yl)ethyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol C19H34O5 详情 详情
(X) 13616 (4-Carboxybutyl)triphenylphosphonium bromide 17814-85-6 C23H24BrO2P 详情 详情
(XI) 13617 (Z)-7-[(1R,2R,3R,5S)-2-[2-(2-Heptyl-1,3-dioxolan-2-yl)ethyl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid C24H42O6 详情 详情
(XII) 13618 isopropyl (Z)-7-[(1R,2R,3R,5S)-2-[2-(2-heptyl-1,3-dioxolan-2-yl)ethyl]-3,5-dihydroxycyclopentyl]-5-heptenoate C27H48O6 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

 

1 Ueno R, Uneo R. 1993. Prostaglandins of the F series. US 5221763
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 13612 (3aR,4R,5R,6aS)-2-oxo-4-(3-oxodecyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C30H36O5 详情 详情
(IX) 66911 (3aR,4R,5R,6aS)-4-(2-(2-heptyl-1,3-dioxolan-2-yl)ethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one   C24H40O6 详情 详情
(XI) 66913 (Z)-isopropyl 7-((1R,2R,3R,5S)-2-(2-(2-heptyl-1,3-dioxolan-2-yl)ethyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate   C32H56O7 详情 详情
(I) 13608 ethyl octanoate; ethyl caprylate 106-32-1 C10H20O2 详情 详情
(II) 66910 dimethyl (3-oxodecyl)phosphonate   C12H25O4P 详情 详情
(III) 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
(IV) 13610 (3aR,4R,5R,6aS)-2-oxo-4-(2-oxoethyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C22H20O5 详情 详情
(V) 13611 (3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-1-decenyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C30H34O5 详情 详情
(VII) 13613 (3aR,4R,5R,6aS)-4-[2-(2-heptyl-1,3-dioxolan-2-yl)ethyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate C32H40O6 详情 详情
(VIII) 13614 (3aR,4R,5R,6aS)-4-[2-(2-Heptyl-1,3-dioxolan-2-yl)ethyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one C19H32O5 详情 详情
(X) 66912 (3aR,4R,5R,6aS)-4-(2-(2-heptyl-1,3-dioxolan-2-yl)ethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol   C24H42O6 详情 详情
Extended Information