154003-23-3

Basic information

• Product Name: Cis -Tosylate
• Synonyms: Cis-[2-(2,4-Dichlorophenyl)-2-(1h-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]Methyl-4-Methylbenzenesulphonate;Cis-[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-Triazol-1-ylmethyl)-1,3-Dioxolan-4-ylMethyl-4- Methlbenzenesulphonate
• CAS NO: 154003-23-3
• Molecular Formula: C₂₀H₁₉Cl₂N₃O₅S
• Molecular Weight: 483.34502
• Mol File: 154003-23-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 184-186 °C(Solv: acetonitrile (75-05-8))
• Boiling Point: 657.7±65.0 °C(Predicted)
• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• PKA: 2.94±0.12(Predicted)
• CAS DataBase Reference: Cis -Tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: Cis -Tosylate(154003-23-3)
• EPA Substance Registry System: Cis -Tosylate(154003-23-3)

Safety Data

• Hazardous Substances Data: 154003-23-3(Hazardous Substances Data)

Usage

General Description

Cis-Tosylate is a chemical compound that is commonly used as a reagent in organic synthesis. It is a derivative of tosylate, which is a functional group containing a tosyl group (SO3C6H4CH3) bonded to an organic molecule. Cis-Tosylate is used to promote a variety of chemical reactions, such as nucleophilic substitution and elimination reactions. It is often used to introduce tosyl groups onto molecules, which can serve as protecting groups for other functional groups, or as leaving groups in substitution reactions. Cis-Tosylate is known for its stability and ease of handling, making it a popular choice for synthetic chemists.

Upstream product

• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 172587-56-3 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 172587-57-4 (2R,4S)-(+)-2-(2,4-dichlorophenyl)-2-<(1H-1,2,4-triazol-1-yl)methyl>-1,3-dioxolane-4-methanol 
• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 

Downstream Products

• 154003-17-5 (2R,4S,2'S)-Itraconazole 
• 154003-18-6 (2R,4S,2'R)-Itraconazole 
• 214117-56-3 (2R,4S)-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[(2S,3R)-3-[(1,1-dimethylethyl)dimethylsiloxy-2-butyl]]-3H-1,2,4-triazol-3-one 
• 214117-53-0 (2R,4S)-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine 
• 199797-85-8 (2R,4S)-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[(2S,3R)-(3-hydroxy-2-butyl)]-3H-1,2,4-triazol-3-one 
• 148626-66-8 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-((1R,2R)-2-hydroxy-1-methyl-propyl)-2,4-dihydro-[1,2,4]triazol-3-one 
• 199797-86-9 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-((1R,2S)-2-hydroxy-1-methyl-propyl)-2,4-dihydro-[1,2,4]triazol-3-one 

Relevant articles and documents

An optical pure itraconazole key intermediate and synthetic method and by the intermediate synthesis of optically pure itraconazole method

The invention disclsoes an optically pure itraconazole key intermediate and synthetic method thereof, and a method for synthesizing the optically pure itraconazole from the intermediate. The method of the invention uses 1-(2,4-dichlorobenzene)-2-(1-methylene-1,2,4-triazole)-1-ketone for preparing the optically pure itraconazole key intermediate, and the optically pure itraconazole key intermediate is used for the preparation of optically pure itraconazole. The method uses easily available raw materials, not only reduces the production cost, but also obtains the product with high purity; through the control of the optical purity of the key intermediate compound VII, the optical purity of the target product itraconazole can be effectively controlled; therefore, the invention has with industrial value.

Impact of absolute stereochemistry on the antiangiogenic and antifungal activities of itraconazole

Itraconazole is used clinically as an antifungal agent and has recently been shown to possess antiangiogenic acitivity. Itraconazole has three chiral centers that give rise to eight stereoisomers. The complete role of stereochemistry in the two activities of itraconazole, however, has not been addressed adequately. For the first time, all eight stereoisomers of itraconazole (1a?h) have been synthesized and evaluated for activity against human endothelial cell proliferation and for antifungal activity against five fungal strains. Distinct antiangiogenic and antifungal activity profiles of the trans stereoisomers, especially 1e and 1f, suggest different molecular mechanisms underlying the antiangiogenic and antifungal activities of itraconazole.

Total synthesis of (2R,4S,2′S,3′R)-hydroxyitraconazole: Implementations of a recycle protocol and a mild and safe phase-transfer reagent for preparation of the key chiral units

A convergent total synthesis of enantiomerically-pure (2R,4S,2′S, 3′R)-hydroxyitraconazole 1b is described. The left dioxolane portion of the molecule was prepared in good yield by the conversion of (S)-10 to the corresponding enantiomerically and diastereomerically-pure acetonide (2R,4R)-3 by a recycle protocol involving diastereoselective crystallization of the tosylate salt, followed by re-equilibration of the mother liquor and crystallization. The right-hand triazolone moeity (2S,3R)-4 was generated by alkyaltion of triazolone 6 with enantiomerically pure cyclic sulfate (4R,5R)-7 under mild and essentially non-hazardous reaction conditions (TDA-1, K 2CO3, acetonitrile).