133775-25-4

Basic information

• Product Name: (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol
• Synonyms: (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol;(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol;2,3-Butanediol, 2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)-;(2R,3R)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butane-2,3-diol
• CAS NO: 133775-25-4
• Molecular Formula: C₁₂H₁₃F₂N₃O₂
• Molecular Weight: 269.2473264
• EINECS: 1592732-453-0
• Mol File: 133775-25-4.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(133775-25-4)
• EPA Substance Registry System: (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol(133775-25-4)

Safety Data

• Hazardous Substances Data: 133775-25-4(Hazardous Substances Data)

Usage

Description

(2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol is a complex organic compound characterized by its unique molecular structure, which features a 2,4-difluorophenyl group and a 1H-1,2,4-triazol-1-yl group attached to a butane-2,3-diol backbone. This molecule is known for its potential applications in various fields due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
(2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol is used as a reagent for preparing phenylisoxazole derivatives, which serve as CYP3A4 inhibitors. CYP3A4 is a crucial enzyme involved in the metabolism of various drugs, and its inhibition can be beneficial in certain therapeutic applications, such as enhancing the efficacy of certain medications or reducing drug-drug interactions.
Additionally, (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol and its derivatives exhibit antifungal activity, making them potentially useful in the development of new antifungal agents to combat fungal infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol can be employed as a building block or intermediate for the synthesis of more complex molecules with diverse applications, such as pharmaceuticals, agrochemicals, or materials science. Its unique structure and functional groups make it a valuable component in the design and synthesis of novel compounds with specific properties and functions.

Upstream product

• 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 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 844879-56-7 (3R)-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)2-butanol 
• 853243-88-6 (2R,3R)-2-(2,4-difluorophenyl)-3-(1-methoxy-1-methylethoxy)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 288-88-0 1,2,4-Triazole 
• 126918-35-2 (1R)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 126918-32-9 (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol 
• 126918-33-0 (1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 

Downstream Products

• 912812-70-5 (2R,3R)-2-(2,4-difluorophenyl)-3-(5-nitro-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912812-72-7 (2R,3R)-3-(5-amino-1H-indazol-1-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912810-58-3 (2R,3R)-2-(2,4-difluorophenyl)-3-(3-methyl-5-nitro-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 912811-29-1 (2R,3R)-2-(2,4-difluorophenyl)-3-(4-fluoro-3-methyl-1H-indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 

Relevant articles and documents

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.

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.

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.