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【结 构 式】

【分子编号】29763

【品名】5-[(3aR,5R,6R,6aR)-3a-methyl-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-6-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoic acid

【CA登记号】

【 分 子 式 】C34H56O6

【 分 子 量 】560.81504

【元素组成】C 72.82% H 10.06% O 17.12%

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:(VI)

Treatment of the optically pure lactone (I) with lithium dimethyl methylphosphonate in tetrahydrofuran gives hemiacetal (II), which is oxidized to the diketone (III) using Jones' reagent in acetone. Then in the key step, compound (III) cyclizes to enone (IV) using potassium carbonate and 18-crown-6 in warm toluene. Lithium dimethyl cuprate addition to enone (IV) in ether gives ketone (V), which is converted to acid (VI) (a 1:1 mixture of E and Z olefins at C-5) using (4-carboxybutyl)triphenylphosphorane in dimethyl sulfoxide. Cleavage of the alcohol-protecting groups in (VI) with an acetic acid-water-tetrahydrofuran mixture followed by chromatography to remove the 5-E isomer affords 9-methylcarbacyclin (VII). Finally, treatment of (VII) with calcium oxide in tetrahydrofuran gives U-61431F (ciprostene calcium).

1 Aristoff, P.A.; Harrison, A.W.; Johnson, P.D.; Synthesis of 9-subtituted cabacyclin analogues. J Org Chem 1983, 48, 5341.
2 Aristoff, P.A.; Practical synthesis of 6a-carbaprostaglandin I2. J Org Chem 1981, 46, 1954.
3 Aristoff, P.A. (Pharmacia Corp.); Composition and process. US 4420632 .
4 Aistoff, P.A.; Ciprostene Calcium. Drugs Fut 1985, 10, 11, 900.
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) 29720 [(dimethoxyphosphoryl)methyl]lithium C3H8LiO3P 详情 详情
(B) 29762 sodium 5-(triphenylphosphoranylidene)pentanoate C23H22NaO2P 详情 详情
(I) 29757 (3aR,4S,5R,6aS)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-one C27H44O6 详情 详情
(II) 29758 dimethyl ((3aR,4S,5R,6aS)-2-hydroxy-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl)methylphosphonate C30H53O9P 详情 详情
(III) 29759 dimethyl 2-oxo-3-((4R,5R)-2-oxo-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]tetrahydro-3-furanyl)propylphosphonate C29H49O10P 详情 详情
(IV) 29760 (3aR,4R,5R)-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-4-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]-3a,4,5,6-tetrahydro-2(3H)-pentalenone C28H44O5 详情 详情
(V) 29761 (3aR,5R,6R,6aR)-3a-methyl-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-6-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2(1H)-pentalenone C29H48O5 详情 详情
(VI) 29763 5-[(3aR,5R,6R,6aR)-3a-methyl-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-6-[(E,3S)-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoic acid C34H56O6 详情 详情
(VII) 29764 5-[(3aS,5R,6R,6aR)-5-hydroxy-6-[(E,3S)-3-hydroxy-1-octenyl]-3a-methylhexahydro-2(1H)-pentalenylidene]pentanoic acid C22H36O4 详情 详情
Extended Information