133775-27-6

Upstream product

• 288-88-0 1,2,4-Triazole 
• 147383-76-4 (R)-2-(2,4-Difluoro-phenyl)-2-((R)-1-methylsulfanyl-ethyl)-oxirane 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 5188-07-8 sodium thiomethoxide 
• 147327-49-9 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-methylsulfanyl-butane-1,2-diol 

Downstream Products

• 182075-03-2 (R)-S-2-<(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)>butyl-S-methyl-N-tosylsulfoximine 
• 182075-12-3 (R)-S-2-<(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)>butyl-S-methylsulfoximine 
• 181885-57-4 (S)-S-2-<(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)>butyl-S-methyl-N-tosylsulfilimine 
• 134779-41-2 (2R,3R)-2-(2,4-difluorophenyl)-3-(methylsulfonyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 

Relevant academic research and scientific papers

Enzyme-catalysed approach to the preparation of triazole antifungals: synthesis of (-)-genaconazole

The work describes a new enzyme-mediated approach to optically active epoxide (2R,3S)-6, which is an important key intermediate in the preparation of single enantiomers of chiral azole antifungals. The conversion of (2R,3S)-6 into (-)-genaconazole is reported as an example of its synthetic relevance.

Optical resolution of dl-threo-2-(2,4-difluorophenyl)-2-[1-(methylthio)ethyl]oxirane: Its application to the synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668

A racemate of threo-2-(2,4-difluorophenyl)-2-[1-(methylthio)ethyl]oxirane was separated into two enantiomers by reaction with a chiral carboxylic acid, followed by separation of the resultant diastereomers, hydrolysis of the ester, and dehydration of the 1,2-diol to the oxirane. This new optical resolution method was applied to the synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668. Thus, the optically active isomer of SM-8668 was prepared efficiently in eight steps from m-difluorobenzene.