SDZ-89-485
1H-1,2,4-三唑-1-乙醇,a-(4-氯苯)-a-(1-环丙基-1-甲基乙基)-,(aR)-Chemical Name: (-)-(R)-alpha-(4-Chlorophenyl)-alpha-(1-cyclopropyl-1-methylethyl)-1H-1,2,4-triazol-1-ethanol; (-)-(R)-2-(4-Chlorophenyl)-3-cyclopropyl-3-methyl-1-(1,2,4-triazol-1-yl)-2-butanol
CAS No. 103183-65-9
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator)
合成路线:Reaction of 1-(4-chlorophenyl)-2-cyclopropyl-2-methyl-1-propanone (I) with lithiated (R)-1-methyl-4-(methylsulfinyl)benzene gives a 3:2 mixture of RR and SR addition product (II),which is separated by chromatography.The RR-diastereomer is reduced with acetyl chloride-sodium iodide in acetone and the resulting thioether (III) is cyclized to the oxirane (IV) by alkylation with triethyloxonium-tetrafluoroborate,followed by treatment with sodium hydroxide.Opening the oxirate with triazole in DMF in the presence of potassium carbonate and 18-crown-6 gives SDZ 89-485.
📌 参考资料/链接：
参考文献标题:Synthesis and structure-activity relationships of SDZ 89-485 and analogues
文献作者:Meingassner,J.G.; Grassberger,M.A.; Schaub,F.
参考来源:Xth Cong Int Soc Human Animal Mycol (Barcelona) 1988,Abst P-153
📄 详细内容
合成路线:Reaction of 1-(4-chlorophenyl)-2-cyclopropyl-2-methyl-1-propanone (I) with lithiated (R)-1-methyl-4-(methylsulfinyl)benzene gives a 3:2 mixture of RR and SR addition product (II),which is separated by chromatography.The RR-diastereomer is reduced with acetyl chloride-sodium iodide in acetone and the resulting thioether (III) is cyclized to the oxirane (IV) by alkylation with triethyloxonium-tetrafluoroborate,followed by treatment with sodium hydroxide.Opening the oxirate with triazole in DMF in the presence of potassium carbonate and 18-crown-6 gives SDZ 89-485.
参考文献标题:SDZ 89-485
文献作者:Grassberger,M.A.
参考来源:Drugs Fut 1989,14(8),772
产品链接: CAS No. 103183-65-9››