合成路线:Reaction of the Grignard reagent derived from 4-chlorobenzyl bromide (I) with allyl bromide (II) gives 4-(4-chlorophenyl)but-1-ene (III),which is epoxidized with peracetic acid in dichloromethane to yield 4-(4-chlorophenyl)-1,2-epoxybutane (IV).Opening of (IV) with the anion of imidazole (V) gives 1-[4-(4-chlorophenyl)-2-hydroxybutyl]imidazole (VI),which is oxidized under Swern conditions to 4-(4-chlorophenyl)-1-(1-imidazolyl)-2-butanone (VII).Ketone (VII) is then reacted with (S)-solketal tosylate [(S)-1,2-O-isopropylideneglycerol-3-O-tosylate] (VIII) in the presence of p-toluenesulfonic acid in toluene to give a mixture of stereoisomers,and (2S,4S)-cis-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-4-(p-toluenesulfonyloxy)methyl-1,3-dioxolane (IX) is then separated by crystallization.Finally,(IX) is treated with 4-aminothiophenol (X) in the presence of potassium carbonate in acetone.
参考文献标题:Process for preparing 1,3-dioxolane derivs
文献作者:Dyson,N.H.; Gardner,J.O.; Prince,A.; Kertesz,D.J.(Syntex (USA),Inc.)
参考来源:JP 1995508002; US 5208331
合成路线:Reaction of the Grignard reagent derived from 4-chlorobenzyl bromide (I) with allyl bromide (II) gives 4-(4-chlorophenyl)but-1-ene (III),which is epoxidized with peracetic acid in dichloromethane to yield 4-(4-chlorophenyl)-1,2-epoxybutane (IV).Opening of (IV) with the anion of imidazole (V) gives 1-[4-(4-chlorophenyl)-2-hydroxybutyl]imidazole (VI),which is oxidized under Swern conditions to 4-(4-chlorophenyl)-1-(1-imidazolyl)-2-butanone (VII).Ketone (VII) is then reacted with (S)-solketal tosylate [(S)-1,2-O-isopropylideneglycerol-3-O-tosylate] (VIII) in the presence of p-toluenesulfonic acid in toluene to give a mixture of stereoisomers,and (2S,4S)-cis-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-4-(p-toluenesulfonyloxy)methyl-1,3-dioxolane (IX) is then separated by crystallization.Finally,(IX) is treated with 4-aminothiophenol (X) in the presence of potassium carbonate in acetone.
参考文献标题:RS-21607-197
文献作者:Prous,J.; Mealy,N.; Castar,J.
参考来源:Drugs Fut 1994,19(2),125
合成路线:Reaction of the Grignard reagent derived from 4-chlorobenzyl bromide (I) with allyl bromide (II) gives 4-(4-chlorophenyl)but-1-ene (III),which is epoxidized with peracetic acid in dichloromethane to yield 4-(4-chlorophenyl)-1,2-epoxybutane (IV).Opening of (IV) with the anion of imidazole (V) gives 1-[4-(4-chlorophenyl)-2-hydroxybutyl]imidazole (VI),which is oxidized under Swern conditions to 4-(4-chlorophenyl)-1-(1-imidazolyl)-2-butanone (VII).Ketone (VII) is then reacted with (S)-solketal tosylate [(S)-1,2-O-isopropylideneglycerol-3-O-tosylate] (VIII) in the presence of p-toluenesulfonic acid in toluene to give a mixture of stereoisomers,and (2S,4S)-cis-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-4-(p-toluenesulfonyloxy)methyl-1,3-dioxolane (IX) is then separated by crystallization.Finally,(IX) is treated with 4-aminothiophenol (X) in the presence of potassium carbonate in acetone.
参考文献标题:Selective inhibition of mammalian lanosterol 14alpha-demethylase: A possible strategy for cholesterol lowering
文献作者:Walker,K.A.M.; Kertesz,D.J.; Rotstein,D.M.; Swinney,D.C.; Berry,P.W.; So,O.Y.; Webb,A.S.; Watson,D.M.; Mak,A.Y.; Burton,P.M.; et al.
参考来源:J Med Chem 1993,36(15),2235-7
产品链接: CAS No. 143484-82-6›› 产品链接: CAS No.143393-27-5››