483340-19-8

Usage

Uses

Used in Pharmaceutical Industry:
(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid is used as an intermediate in the synthesis of Isavuconazole (I777830) for the treatment of invasive fungal infections. Its role in the synthesis process is essential, as it contributes to the development of a potent antifungal agent that can effectively combat various fungal pathogens.
Used in Antifungal Applications:
(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid is used as a key component in the development of Isavuconazole, a triazole-based antifungal agent. (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid is effective against a wide range of invasive fungal infections, including those caused by Candida and Aspergillus species. Its incorporation into Isavuconazole enhances the drug's ability to target and disrupt the fungal cell membrane, leading to the inhibition of fungal growth and the resolution of infections.

Upstream product

• 944473-05-6 (2R,3R)-3-[3-(2,5-difluorophenyl)-3,4-epoxy-2-methyl]butanoic acid 
• 41253-21-8 sodium triazole 
• 1157938-97-0 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 

Downstream Products

• 241479-75-4 (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 
• 241479-74-3 (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile 
• 241479-67-4 Isavuconazole 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES

The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

PROCESS FOR THE MANUFACTURE OF ISAVUCONAZOLE OR RAVUCONAZOLE

The invention relates to a process for the manufacture of diastereomerically and enantiomerically enriched triazole compounds isavuconazole and ravuconazole, comprising a Reformatsky reaction between a ketone and a 2-halozincpropionate ester, followed by

Method for resolving racemic body of intermediate compound of Isavuconazole

The invention discloses a novel method for resolving a racemic body of an intermediate compound of Isavuconazole. According to the novel method, R(+)-alpha-methylbenzylamine is adopted as a resolving reagent, and (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxyl-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid with high optical purity is obtained. According to the novel method for resolving the racemic body of the intermediate compound of the Isavuconazole, disclosed by the invention, the steps are simple, the yield is relatively high, and (2R, 3R)-3-(2,5-difluorophenyl)-3-hydroxyl-2-methyl-4-(1H-1,2,4-triazol-1-yl) butanoic acid with high optical purity is obtained through resolution; and meanwhile, the resolving reagent, i.e., R(+)-alpha-methylbenzylamine can be recovered and reused, so that the cost is reduced, the implementation of industrialized amplified production is facilitated, and the novel method has a very good industrial application prospect.

PROCESS FOR THE MANUFACTURE OF ISAVUCONAZOLE OR RAVUCONAZOLE

The invention relates to a process for the manufacture of diastereomerically and enantiomerically enriched triazole compounds isavuconazole and ravuconazole, comprising a Reformatsky reaction between a ketone and a 2-halozincpropionate ester, followed by a resolution step, preferably an enzymatic resolution with an esterase enzyme.

Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents

The Ni(acac)2 catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of