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【结 构 式】

【分子编号】36244

【品名】methyl 7-[(1R,2R,3R,5S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-hydroxycyclopentyl]-7-oxoheptanoate

【CA登记号】

【 分 子 式 】C33H64O6Si2

【 分 子 量 】613.03856

【元素组成】C 64.66% H 10.52% O 15.66% Si 9.16%

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:(III)

5epsilon-lodo-9-deoxy-6epsilon,9alpha-epoxy-PGF1alpha (I) is protected with tert-butyldimethylsilyl chloride in DMF containing imidazole yielding the disilylated compound (II), which is treated with diazabicyclononane (DBN) in DMF to give the hydroxy keto ester (III). Acetylation of (III) with acetic anhydride in pyridine affords the corresponding acetoxy compound (IV), which by hydrolysis with NaOH affords the free hydroxy acid (V). Oxidation of (V) with Jones' reagent yields the diketonic acid (VI), which by cyclization with aniline (A) in pyridine - methanol followed by esterification with diazomethane is converted into the protected ester (VII). Elimination of the silyl groups of (VII) with tetrabutylanimonium fluoride in THF gives the methyl ester of U-60,257 (VIII), which is finally hydrolyzed with NaOH in methanol.

1 Smith, H.W. (Pharmacia Corp.); Nitrogen-containing prostacyclin analogues, their preparation and compsns. containing them. EP 0029341 .
2 Sneddon, J.M.; Castaner, J.; Serradell, M.N.; Blancafort, P.; U-60,257. Drugs Fut 1983, 8, 10, 877.
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) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(I) 36242 methyl 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C21H35IO5 详情 详情
(II) 36243 methyl 5-[(3aR,4R,5R,6aS)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C33H63IO5Si2 详情 详情
(III) 36244 methyl 7-[(1R,2R,3R,5S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-hydroxycyclopentyl]-7-oxoheptanoate C33H64O6Si2 详情 详情
(IV) 36245 methyl 7-[(1R,2R,3R,5S)-5-(acetoxy)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)cyclopentyl]-7-oxoheptanoate C35H66O7Si2 详情 详情
(V) 36246 7-[(1R,2R,3R,5S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-hydroxycyclopentyl]-7-oxoheptanoic acid C32H62O6Si2 详情 详情
(VI) 36247 7-[(1S,2R,3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-5-oxocyclopentyl]-7-oxoheptanoic acid C32H60O6Si2 详情 详情
(VII) 36248 methyl 5-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-((E,3S)-3-[[tert-butyl(dimethyl)silyl]oxy]-1-octenyl)-1-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrol-2-yl]pentanoate C39H65NO4Si2 详情 详情
(VIII) 36249 methyl 5-[(4R,5R)-5-hydroxy-4-[(E,3S)-3-hydroxy-1-octenyl]-1-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrol-2-yl]pentanoate C27H37NO4 详情 详情
Extended Information