133825-95-3

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 563-76-8 α-bromopropionyl bromide 
• 5188-07-8 sodium thiomethoxide 
• 135206-83-6 2-bromo-1-(2,4-difluorophenyl)-1-propanone 

Relevant academic research and scientific papers

Stereoselective synthesis of antifungal sulfoximines, novel triazoles II

Novel triazole derivatives with N-substituted sulfoximine moiety were synthesized and evaluated for antifungal activity. These compounds showed only significantly weak activity and the N-H sulfoximine moiety was extremely important for the activity. A more practical and effective stereoselective synthesis of N-H sulfoximine, (R)-S-2-[(2R,3R)-3-(2,4-difluorophenyl)-3- hydoroxy-4-(1H-1,2,4-triazol-1-yl)]butyl-S-methylsulfoximine (1), which was considered to be the most promising compound, has been developed.

Stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668)

The stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2-(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent and aqueous alkaline solution.