170863-34-0

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-Methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyraMide is used as an intermediate in the synthesis of triazole antifungal agents. Its unique structure allows it to be a key component in the development of new antifungal medications, which can be effective against a range of fungal infections.
Chemical Properties:
The compound presents as an off-white foam, indicating its physical state and appearance. This characteristic can be relevant for its handling, storage, and further chemical processing in the context of its applications.

Upstream product

• 170862-36-9 (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 166948-49-8 (2R,3R)-3-[3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid 
• 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 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 60899-79-8 diethyl dithiophosphate 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 135270-13-2 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 

Downstream Products

• 170863-35-1 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-[4-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 1316741-78-2 4-{2-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-4-yl-propyl]}(4-[14]C-thiazol-4-yl)-benzonitrile 
• 1316741-92-0 4-{2-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-4-yl-propyl]thiazol-4-yl}[Ar-⁽¹³⁾C₆]benzonitrile 
• 207224-81-5 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-{4-[4-(2H-tetrazol-5-yl)-phenyl]-thiazol-2-yl}-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 207224-83-7 (2R,3R)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-3-{4-[4-(1H-[1,2,4]triazol-3-yl)-phenyl]-thiazol-2-yl}-butan-2-ol 
• 368421-60-7 4-{2-[(1R,2R)-2-(2,4-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-thiobenzamide 
• 182760-06-1 ravuconazole 

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.

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.

Process for the manufacture of enantiomerically pure antifungal azoles as ravuconazole and isavuconazole

A new technical process for preparation of enantiomerically pure antifungal compounds of formula I by resolution of the racemates has been disclosed.

Improved chiral synthesis of ravuconazole

A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate. Copyright Taylor & Francis Group, LLC.

Azole antifungal agents, processes for the preparation thereof, and intermediates

A compound represented by the general formula: wherein R1 and R2 denote a halogen atom or hydrogen atoms; R3 means a hydrogen atoms or lower alkyl group; r and m stand for 0 or 1; A is N or CH; W denotes an aromatic ring or a condensed ring thereof; X means another aromatic rings, an alkanediyl group, an alkenediyl group, or an alkynediyl group; Y stand for -S-, etc.; Z denotes a hydrogen atom, etc., or a salt thereof, and intermediates thereof or a salt thereof as well as processes for the preparation thereof, and pharmacetical composition suitable for use as an antifungal agent.

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.

Synthesis of 14C-labelled ER-30346, a novel antifungal triazole

ER-30346 is a new orally active antifungal triazole which has potent, broad spectrum antifungal activity, and good safety profile. It was synthesized labelled in the phenyl ring of the benzonitrile moiety with carbon-14, starting from 4-acetyl[ring-U-14C]benzonitrile, according to the method illustrated in Scheme 1. 14C-labelled ER-30346 having a specific activity of 1.89 Bq/mmol was obtained in 65.4% overall radiochemical yield, with a radiochemical purity of 99.7%.