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【结 构 式】 
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【分子编号】44371 【品名】(4S)-4-hydroxy-4-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-1-butanone 【CA登记号】 |
【 分 子 式 】C24H32O9S 【 分 子 量 】496.57868 【元素组成】C 58.05% H 6.5% O 29% S 6.46% |
合成路线1
该中间体在本合成路线中的序号：(III)The selective monoreduction of the already known (see scheme 14265002a) 1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)butane-1,4-dione (I) with LiAlH(O-t-Bu)3 in THF gives the hydroxybutanone (II) as a racemic mixture that is separated by esterification with (-)-(R)-mandelic acid, separation of diastereomers and hydrolysis with KOH in ethanol yielding (S)-(III) and (R)-(IV) as pure enantiomers. The reduction of both (S)-(III) and (R)-(IV) with NaBH4 in hot ethanol gives (S)-(V) and (R)-(VI) diols that are cyclized by means of TFA in chloroform to afford trans-(S,S)- and trans-(R,R)-target compounds. Both compounds are impurified with about 25% of the corresponding cis-isomer that is separated by chromatography.
| 【1】 Chabala, J.C.; Buglanesi, R.L.; Ponpipom, M.M.; Enantioselective cyclization of chiral butane-1, 4-diols to chiral tetrahydrofurans: Synthesis of chiral trans-2-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (L-659,989), a potent PAF-receptor antagonist. Tetrahedron Lett 1988, 29, 48, 6211. |
| 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) | 44366 | 1-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione | C24H30O9S | 详情 | 详情 | |
| (II) | 44367 | 4-hydroxy-4-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-1-butanone | C24H32O9S | 详情 | 详情 | |
| (III) | 44371 | (4S)-4-hydroxy-4-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-1-butanone | C24H32O9S | 详情 | 详情 | |
| (IV) | 44372 | 5-methoxy-1,1-bis(phenylsulfanyl)-3,4-dihydro-2(1H)-naphthalenone | C23H20O2S2 | 详情 | 详情 | |
| (V) | 44373 | tert-butyl 2-(bromomethyl)acrylate | C8H13BrO2 | 详情 | 详情 | |
| (VI) | 44374 | tert-butyl 2-[[8-methoxy-3-oxo-4,4-bis(phenylsulfanyl)-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]acrylate | C31H32O4S2 | 详情 | 详情 |