134779-41-2

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R)-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1,2,4-triazol-1-yl)butan-2-ol is used as a potential active pharmaceutical ingredient for its presence of the triazolyl group, which is commonly found in antifungal medications, indicating its use for treating fungal infections.
Used in Agricultural Industry:
The presence of the difluorophenyl group in (2R,3R)-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1,2,4-triazol-1-yl)butan-2-ol suggests its potential use as a pesticide or herbicide, contributing to crop protection and management.
Used in Chemical Industry:
Due to its unique structure and the presence of various functional groups, (2R,3R)-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1,2,4-triazol-1-yl)butan-2-ol may have applications in the development of new chemical compounds or processes within the chemical industry.

InChI:InChI=1/C13H15F2N3O3S/c1-9(22(2,20)21)13(19,6-18-8-16-7-17-18)11-4-3-10(14)5-12(11)15/h3-5,7-9,19H,6H2,1-2H3/t9-,13-/m0/s1

Upstream product

• 124627-86-7 (2R^*,3S^*)-2-(2,4-Difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane 
• 132507-89-2 threo-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 182699-15-6 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-methanesulfonyl-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 147383-77-5 (S)-2-(2,4-Difluoro-phenyl)-2-((S)-1-methylsulfanyl-ethyl)-oxirane 
• 135133-23-2 (3R)-2-(2,4-difluorophenyl)-3-(tetrahydropyran-2-yloxy)-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 182699-19-0 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-methylsulfanyl-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 103016-00-8 threo-2-(2,4-difluorophenyl)-3-methylthio-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 7440-44-0 pyrographite 
• 546-68-9 titanium(IV) isopropylate 
• 75-34-3 1,1-dichloroethane 
• 7631-95-0 sodium molybdate dihydrate 
• 10213-10-2 sodium tungstate (VI) dihydrate 
• 182699-17-8 (2R,3R)-2-(2,4-difluorophenyl)-2-hydroxymethyl-3-methyloxirane 
• 182699-20-3 Methanesulfonic acid (2R,3R)-2-(2,4-difluoro-phenyl)-3-methyl-oxiranylmethyl ester 

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.

N-benzylazolium derivatives

N-Benzylazolium derivatives of the general formula (I), STR1 wherein Q is the remainder of an azole compound of the formula II STR2 possessing antifungal activity; Z is nitrogen or methine; R1 and R2 are each independently a hydrogen

Preparations of antifungal Sch 42427/SM 9164: Preparative chromatographic resolution, and total asymmetric synthesis via enzymatic preparation of chiral α-hydroxy arylketones

Efficient approaches towards the preparation of chiral azole antifungals Sch 42427/SM 9164 (1) via large scale chromatographic separation of its enantiomers, or via enzymatic syntheses of key chiral intermediates α-hydroxy arylketones 5 in excellent enantiomeric excesses (ees) are described.

Asymmetric synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668

SM-9164, a biologically active enantiomer of antifungal agent SM-8668, was prepared by asymmetric synthesis in 10 steps in 13% overall yield from commercially available 2-chloro-1-(2,4-difluorophenyl)ethanone. The crucial steps were Katsuki-Sharpless asymmetric epoxidation of the (E)-allylic alcohol and epimerization of the erythro-sulfone to the desired threo-isomer under basic conditions.

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.

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.

Selective production of threo-epoxy compounds

A process for selective production of a threo-epoxy compound of the formula: STR1 wherein Ar is a substituted or unsubstituted phenyl group and R1 and R2 are each a lower alkyl group, which comprises reacting a ketone compound of the

Optical resolution of sulfone derivatives

A method for the optical resolution of sulfone derivatives, which comprises reacting a mixture of the d- and 1-isomers of a sulfone derivative of the formula: wherein X1 and X2 are each and independently a hydrogen atom or a halogen atom with optically active 10-camphorsulfonic acid to make a mixture of two kinds of diastereomer salts between them, isolating one of the diastereomer salts from said dia-stereomer salt mixture on the difference of the diastereomer salts in solubility and decomposing the isolated dia-stereomer salt.

Process for preparation of sulfone derivatives

A process for preparing sulfone derivatives of the formula: wherein R1 and R2 are each a hydrogen atom, a lower alkyl group or a substituted or unsubstituted cyclo(lower)alkyl, cyclo(lower)alkylmethyl, lower alkenyl, heterocyclic, aryl or ar(lower)alkyl g