135270-05-2

Basic information

• Product Name: (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol
• Synonyms: (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol;(2S,3S)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol;(3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol
• CAS NO: 135270-05-2
• Molecular Formula: C₁₂H₁₃F₂N₃O₂
• Molecular Weight: 269.2473264
• EINECS: -0
• Mol File: 135270-05-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(135270-05-2)
• EPA Substance Registry System: (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(135270-05-2)

Safety Data

• Hazardous Substances Data: 135270-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol is used as an active ingredient in antifungal medications for the treatment of various fungal infections. Its application is based on its ability to effectively target and inhibit the synthesis of ergosterol, which is essential for the structural integrity and function of fungal cell membranes, leading to the eradication of the infecting fungi.
Used in Clinical Practice:
In clinical practice, (2S,3S)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol is utilized as a therapeutic agent for managing fungal infections due to its demonstrated efficacy and safety profile. Its relatively low toxicity and the favorable side effects associated with its use contribute to its widespread acceptance and application in treating a range of fungal diseases.

Upstream product

• 288-88-0 1,2,4-Triazole 
• 126918-35-2 (1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 247196-88-9 C₁₆H₁₄F₂O₂ 
• 137035-03-1 [(2S,3R)-2-(2,4-Difluoro-phenyl)-3-methyl-oxiranyl]-methanol 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 1774-47-6 trimethylsulfoxonium iodide 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 127001-03-0 (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 274682-91-6 1-(2,4-difluorophenyl)-2-propanone 
• 367-25-9 2,4-difluorophenylamine 
• 135267-12-8 2-((R)-1-((R)-2-(2,4-difluorophenyl)oxiran-2-yl)ethoxy)tetrahydro-2H-pyran 

Downstream Products

• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 126917-19-9 (E)-1-[(4S,5S)-5-(2,4-Difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-3-(4-trifluoromethyl-phenyl)-propenone 
• 124627-86-7 1-[(2S,3S)-2-(2,4-Difluoro-phenyl)-3-methyl-oxiranylmethyl]-1H-[1,2,4]triazole 
• 126916-57-2 (2R*,3R*)-3-Amino-2-(2,4-difluoropropyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 126916-57-2 (2R,3S)-3-Amino-2-(2,4-difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 132507-89-2 (2R,3S)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butane-2,3-diol 
• 126916-45-8 (4R*,5R*)-5-(2,4-Difluorophenyl)-4-methyl-5-<(1H-1,2,4-triazol-1-yl)methyl>oxazolidine 
• 126916-45-8 1-[(4R,5S)-5-(2,4-Difluoro-phenyl)-4-methyl-oxazolidin-5-ylmethyl]-1H-[1,2,4]triazole 
• 126945-34-4 Methanesulfonic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 132507-72-3 (4R^*,5R^*)-5-(2,4-Difluorophenyl)-4-methyl-3-(5-methyl-4-hexenoyl)-5-<(1H-1,2,4-triazol-1-yl)methyl>oxazolidine 
• 126916-84-5 (4-Chloro-phenyl)-[(4R,5R)-5-(2,4-difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-methanone 
• 126917-17-7 (E)-3-(4-Chloro-phenyl)-1-[(4S,5S)-5-(2,4-difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-propenone 
• 126916-89-0 [(4R,5R)-5-(2,4-Difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-(4-trifluoromethyl-phenyl)-methanone 
• 126916-89-0 [(4S,5R)-5-(2,4-Difluoro-phenyl)-4-methyl-5-[1,2,4]triazol-1-ylmethyl-oxazolidin-3-yl]-(4-trifluoromethyl-phenyl)-methanone 

Relevant articles and documents

NOVEL METHOD FOR PREPARATION OF EPOXYTRIAZOLE DERIVATIVES

The present invention relates to novel processes for preparing epoxytriazole derivatives. The method of claim 1, further comprising the step of adding a base to the intermediate compound. The present invention relates to an epoxytriazole derivative and a manufacturing method thereof. Chemical Formula 1. Here, Ar denotes C. 6 -C10 Aryl group or C aryl group2 -C9 The aryl group 1 -4 is substituted or unsubstituted, and when 2 or more halogen is substituted, the heteroaryl group may be the same as or different from each other, and the heteroaryl group is represented by 1 -4 fluorine, chlorine, or C. 1 -C3 Substituted or unsubstituted alkyl groups, and fluorine, chlorine, or C. 1 -C3 When more than 2 substituents are substituted, each of these substituents may be the same or different and may be different from each other. The A is C. 1 -C3 Represents an alkyl group, and the R represents an alkyl group. 1 And R2 Is a methyl group or an ethyl group.

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

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.

Triazole alcohol derivative as well as preparation method and application thereof

The invention relates to a triazole alcohol derivative as well as a preparation method and application thereof. The chemical structure of the triazole alcohol derivative is shown as a formula I, R1 represents a benzene ring or a substituted benzene ring, and substituent groups of the substituted benzene ring can be located at all positions of the benzene ring, can be mono-substituted or multi-substituted, and can be selected from a) halogen which is F and Cl; b) an electron withdrawing group which is cyano or trifluoromethyl; c ) a lower alkyl of 1-4 carbon atoms or a halogen substituted loweralkyl; and d) lower alkoxy of 1-4 carbon atoms or halogen substituted lower alkoxy. The compound of the invention has strong antifungal activity, has the advantages of low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal drugs.

Triazole alcohol derivative, and preparation method and application thereof

The invention relates to a triazole alcohol derivative, and a preparation method and an application thereof. The chemical structure of the triazole alcohol derivative is represented by formula I, A inthe formula I represents a benzene ring or a substituted benzene ring, and the substituent group of the substituted benzene ring can be located at each position of the benzene ring, is monosubstituted or polysubstituted, and is selected from: a) halogen which is F, Cl, Br or I; b) an electron-withdrawing group, wherein the electron withdrawing group is a cyano group, a nitro group or a trifluoromethyl group; c) a C1-4 low alkyl group or a halogen-substituted low alkyl group; and d) a C1-4 low alkoxy group or a halogen-substituted low alkoxy group. The compound has the advantages of high antifungal activity, low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal medicines.

Synthesis method of efinaconazole intermediate

Belonging to the field of biomedical industry, the invention discloses a synthesis method of an efinaconazole intermediate VI. The method includes: taking benzyl as a hydroxyl protecting group to generate a new compound II, then carrying out Grignard reaction, epoxidation reaction and epoxy ring-opening reaction on the compound II, and finally carrying out deprotection reaction to obtain the efinaconazole intermediate VI. The preparation method provided by the invention adopts benzyl as the hydroxyl protecting group, improves the problem of easy ring opening of tetrahydropyrane protecting group under an acidic condition in an original method, and at the same time has the advantages of good product purity and high yield.

METHOD FOR PRODUCING ALCOHOL COMPOUND

A high-purity alcohol compound can be obtained by a method comprising passing a solution containing an ester compound and methanol and/or ethanol through a column packed with an anion exchange resin having methoxide and/or ethoxide as a counter anion to g

METHOD FOR PRODUCING TRIAZOLE COMPOUND

PROBLEM TO BE SOLVED: To provide a novel method for producing a triazole compound useful as a pharmaceutical intermediate. SOLUTION: A production method includes reacting a lactic acid derivative with thionyl chloride, then reacting it with 1,3-difluoro benzene in the presence of Al chloride to obtain a ketone derivative, which is turned into an olefin with a Wittig reagent to be derived into compound (2), and it is then turned into an epoxy and a triazole to be derived into compound (1). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Method for preparing efinaconazole intermediate

The invention discloses a method for preparing an efinaconazole intermediate. The method comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound as shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant to prepare a compound as shown in the formula 3, wherein R is halogen or 1,2,4-triazolyl, and R is hydrogen or methyl. The method is green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formula 2 and the formula 3 are as shown in the description.

Efinaconazole, preparation method of efinaconazole intermediate and efinaconazole intermediate

The invention discloses efinaconazole, a preparation method of an efinaconazole intermediate and the efinaconazole intermediate. A preparation method of efinaconazole comprises the following step: in a solvent, under the action of a reducing agent, performing reductive amination reaction on a compound shown in the formula 4 and a compound shown in the formula B. The invention also provides the efinaconazole intermediate shown in the formula 4 and the preparation method thereof, and the preparation method comprises the following step: performing oxidizing reaction on a compound shown in the formula 3 to obtain the compound shown in the formula 4. A preparation method of the compound shown in the formula 3 comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant. The efinaconazole and the preparation method of the efinaconazole intermediate are green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formulas 2, 3, 4 and B are as shown in the description.