160709-02-4

Basic information

• Product Name: D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-
• Synonyms: D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-;[5-(2,4difluoro- phenyl)-5-[1,2,4] triazole-1yl-methyltetrahydrofuran-3-yl]-Methanol;2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxymethyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol;3R, 5R-[5-(2,4-Difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-yl]-methanol;((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methanol;(-)-(5R-cis)-5-(2,4-Difluoro-phenyl)-5-[(1H-1,2,4-triazole-1-yl)methyl]-tetrahydro-3-furanmethanol
• CAS NO: 160709-02-4
• Molecular Formula: C₁₄H₁₅F₂N₃O₂
• Molecular Weight: 295.2846064
• EINECS: -0
• Mol File: 160709-02-4.mol

Chemical Properties

• Boiling Point: 457.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.81±0.10(Predicted)
• CAS DataBase Reference: D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-(160709-02-4)
• EPA Substance Registry System: D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-(160709-02-4)

Safety Data

• Hazardous Substances Data: 160709-02-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxymethyl)-1-(1H-1,2,4-triazol-1-yl)is used as a building block for the synthesis of key intermediates towards the synthesis of highly active azole antifungals, such as Sch 51048, Sch 56592, and Sch 45012. These antifungal agents are effective against a wide range of fungal infections and are crucial in the treatment of various medical conditions.
Additionally, D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxymethyl)-1-(1H-1,2,4-triazol-1-yl)is also an impurity/intermediate for posaconazole (P689600), which is a potent antifungal drug used to treat severe fungal infections, particularly in immunocompromised patients. The compound plays a significant role in the development and production of these life-saving medications, contributing to the advancement of medical treatments for fungal infections.

Upstream product

• 182210-71-5 ((3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-yl)methanol 
• 192448-07-0 2-methylpropanoic acid [(2S)-4-(2,4-difluorophenyl)-2-hydroxymethyl-4-penten-1-yl] ester 
• 41253-21-8 sodium triazole 
• 110931-77-6 4-(2,4-difluorophenyl)-4-oxobutanoic acid 
• 165115-70-8 4-(2,4-difluorophenyl)-pent-4-enoic acid 
• 159276-62-7 diethyl 2-[2-(2,4-difluorophenyl)-2-propen-1-yl]-1,3-propanedioate 
• 156570-10-4 1-(1-chloromethylethenyl)-2,4-difluorobenzene 
• 165115-73-1 2-[2-(2,4-difluorophenyl)-2-propene-1-yl]-1, 3-propanediol 
• 149509-28-4 1-Chloro-2-(2,4-difluorophenyl)-3-trimethylsilyl-2-propanol 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 1350560-52-9 C₁₆H₁₉F₂IO₃ 
• 149809-50-7 Acetic acid (2R,4R)-4-(2,4-difluoro-phenyl)-4-hydroxy-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentyl ester 
• 149809-38-1 (R)-4-(2,4-Difluoro-phenyl)-2-hydroxymethyl-5-[1,2,4]triazol-1-yl-pentane-1,4-diol 

Downstream Products

• 170985-86-1 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one 
• 171228-49-2 posaconazote 
• 175712-02-4 ((3S,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl 4-chlorobenzenesulfonate 
• 149809-43-8 (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 

Relevant articles and documents

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE

The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.

IMPROVED PROCESS FOR THE PREPARATION OF ((3S,5R)-5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-5-(2,4-DIFLUOROPHENYL)TETRAHYDROFURAN-3-YL)METHYL-4-METHYLBENZENESULFONATE

The present invention relates to process for the preparation of ((3S,5R)-5-((lH-l,2,4- triazol- 1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzene sulfonate compound of formula- 1 through novel intermediates. Further the said compound of formula- 1 is useful as a key intermediate for the preparation of Posaconazole.

Purification of Posaconazole Intermediates

The present invention relates to a process for the purification of chiral compounds, in particular to the purification of a chiral compound of formula (XI) which may be used as intermediate for the preparation of antifungal agents, preferably posaconazole.

Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof

A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)

PREPARATION OF POSACONAZOLE INTERMEDIATES

The present invention relates to process for the preparation of a chiral compound of formula (IX) or a salt thereof, wherein Y1and Y2 are independently F or C1, preferably F, the crystalline compound of formula (IX) as such, and its use for the preparation of an antifungal agent.

PURIFICATION OF POSACONAZOLE AND POSACONAZOLE INTERMEDIATES

The present invention relates to a process for the preparation of a hydrogen chloride (HC1) salt of a compound of formula (I) wherein Y1 and Y2 are independently F or C1, preferably F, said compound of formula (I) containing the cis-isomer and the trans-isomer, wherein the process comprises (1) providing the compound of formula (I) comprised in a first suitable solvent; and (2) treating the compound of formula (I) comprised in the first suitable solvent with HC1 comprised in a second suitable solvent to obtain the HC1 salt of the compound of formula (I)·

PROCESS FOR PREPARING POSACONAZOLE AND INTERMEDIATES THEREOF

The present invention relates to an industrially advantageous process for the preparation of tetrahydrofuran antifungals preferably posaconazole of formula I. The present invention further relates to improved processes for preparing key and novel intermediates useful in the preparation of posaconazole. The present invention further relates to improved processes for preparing the compound of formula II, a key intermediate in the preparation of posaconazole.

Concise asymmetric routes to 2,2,4-trisubstituted tetrahydrofurans via chiral titanium imide enolates: Key intermediates towards synthesis of highly active azole antifungals Sch 51048 and Sch 56592

Two complimentary approaches to the key (-)-(2R)-cis-tosylate 1 and its (+)-(2S)-enantiomer 15 via generation of chiral imide enolates having a 2,2-disubstituted olefin functionality in the β-position, are described. In a 'protecting group free' sequence, reaction of the titanium enolate generated from (4R)-benzyl-2-oxazolidinone derived imide 5b with s-trioxane provided a convenient intermediate 19 which could be directly subjected to 2,4-diastereoselective iodocyclization.

HIGHLY STEREOSELECTIVE ACCESS TO NOVEL 2,2,4-TRISUBSTITUTED TETRAHYDROFURANS BY HALOCYCLIZATION: PRACTICAL CHEMOENZYMATIC SYNTHESIS OF SCH 51048, A BROAD-SPECTRUM ORALLY ACTIVE ANTIFUNGAL AGENT

A convenient synthesis of (-)-(2R)-cis-tosylate 2 is reported via stereoselective 5-exo iodocyclization of the optically active 2,2-disubstituted olefin 9a.Enzymatic desymmetrization of the homoallylic diol 4 with Novo SP435 allowed optimal pro-(S) selectivity to provide the desired (-)-(S)-monoacetate 9a.Under the irreversible reaction conditions, the presence of a bulky aryl substituent on the 2,2-disubstituted olefin seems to determine stereochemical outcome of these halocyclizations.

PPL-catalyzed enzymatic asymmetrization of a 2-substituted prochiral 1,3-diol with remote chiral functionality: Improvements toward synthesis of the eutomers of SCH 45012

Porcine pancreatic lipase (PPL) catalysis has been used to establish both stereocenters of the cis-(tetrahydrofuranylmethyl) tosylate 4. In addition to the enzymatic differentiation of the hydroxyl groups of the pro-chiral 1,3-diol segment of 2, successful enzymatic resolution of the racemic diol 10 provided an alternate route to the important precursor 1.