126918-35-2

Usage

Uses

Used in Pharmaceutical Industry:
(1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol is used as a chiral building block for the synthesis of pharmaceutical compounds due to its unique structure and the presence of fluorine atoms, which can influence the compound's lipophilicity and metabolic stability.
Used in Organic Synthesis:
(1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol serves as an intermediate in organic synthesis, particularly for the preparation of complex organic molecules that require chiral centers or specific functional groups, such as those found in pharmaceuticals or agrochemicals.
Used in Materials Science:
(1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol may be utilized in the development of new materials with specific properties, such as chiral polymers or materials with tailored electronic or optical characteristics, given its unique molecular structure and the potential for further functionalization.

Upstream product

• 25596-24-1 trimethyloxosulfonium bromide 
• 126918-16-9 (R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one 
• 5034-06-0 trimethyl sulfoxonium chloride 
• 1774-47-6 trimethylsulfoxonium iodide 
• 1610930-73-8 (2S,3S)-4-chloro-3-(2,4-difluorophenyl)-3-((trimethylsilyl)-oxy)butan-2-ol 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 
• 861718-83-4 (S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 127001-03-0 (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 126918-33-0 (1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 126918-15-8 (S)-2-(p-toluenesulfonyloxy)-2',4'-difluoropropiophenone 
• 138373-68-9 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanyl-butan-2-ol 
• 126918-32-9 (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol 

Downstream Products

• 135270-14-3 (R)-1-[(R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl methanesulfonate 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 126917-48-4 (2R,3R)-3-Azido-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 126918-36-3 [(1R)-1-[(2S)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]methanesulfonate 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 155432-64-7 2-<(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING EPOXY ALCOHOL COMPOUND

A compound represented by formula (II): (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): that is useful for production of an antifungal agent.

An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)

A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.

Method of purifying 3-phenyl-3,4-epoxy-2-butanol derivatives by liquid-liquid extraction

An epoxy compound of the formula (1): wherein, R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, and Ar represents an optionally substituted aromatic group, can be purified by dissolving a crude product containing the epoxy compo

PROCESS FOR PRODUCING EPOXYTRIAZOLE COMPOUND AND INTERMEDIATE THEREFOR

The present invention provides a compound of the formula (I); wherein Ar represents difluorophenyl group, which is useful as an intermediate in a process for producing an epoxytriazole compound of the formula (VII); wherein Ar represents difluorophenyl group, which is a synthetic intermediate of antifungal agents. The present invention also provides a process for producing a compound of the formula (VII) which comprises epoxydation step, deprotection step, reaction step with a compound represented by RSO2X, and reaction step with 1,2,4-triazole; or comprises epoxydation step, reaction step with 1,2,4-triazole, deprotection step, reaction step with a compound represented by RSO2X and treatment step by a base.

OPTICALLY ACTIVE HALOHYDRIN DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY ALCOHOL DERIVATIVE FROM THE SAME

The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxyalcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps. A process for producing an optically active epoxy alcohol derivative includes allowing an optically active α-substituted propionate derivative to react with a haloacetic acid derivative in the presence of a base to prepare an optically active haloketone derivative, allowing the resulting haloketone derivative to react with an aryl metal compound to stereoselectively prepare a halohydrin derivative, eliminating a substituent for the hydroxy group of the halohydrin derivative, and performing epoxidation with a base. Furthermore, a process for producing an intermediate for a triazole antifungal agent includes allowing a halohydrin derivative to react with a triazole sulfonamide, the process including a small number of steps.

Production methods of epoxytriazole derivative and intermediate therefor

An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base. wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.

Optically active antifungal azoles. VII. Synthesis and antifungal activity of stereoisomers of 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1- methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-[4-(2,2,3,3- tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (TAK-187)

2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4- triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluopropoxy)phenyl]-3(2H,4H)-1,2,4- triazolone [(1R,2R)-1: TAK-187] is a new antifungal agent selected as a candidate for clinical trials. The three stereoisomers [(1S,2S)-, (1R,2S)- and (1S,2R)-1] of this compound were prepared to clarify the relationship between the stereochemistry and the biological activities. In vitro and in vivo assays of antifungal activity revealed TAK-187 [(1R,2R)-1] is the most potent among the four stereoisomers. Furthermore, TAK-187 was found to exert a strong and selective inhibitory effect on the sterol synthesis in Candida albicans as compared with that in rat liver.

Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones

A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.

Optically active tetrazole compounds, and fungicidal compositions thereof

An optically active azole compound of the formula (I): STR1 wherein R1 and R2 are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R3 is a hydrogen atom or an acyl group; Q is CH or N; --NA is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R1 and R2 is an optionally substituted nitrogen-containing heterocyclic group when --NA is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.

Payne rearrangement route to the optically active oxirane precursor for the preparation of triazole antifungals

Optically active epoxide 1, an important intermediate for the preparation of antifungal triazole-amides 2, was synthesized starting from the (S)-lactic acid-derived ketone 9 and taking advantage of the Payne rearrangement of the epoxyalcohol 8.