199797-85-8

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 199797-85-8
• Molecular Weight: 721.643
• Mol File: 199797-85-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(199797-85-8)
• EPA Substance Registry System: (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(199797-85-8)

Safety Data

• Hazardous Substances Data: 199797-85-8(Hazardous Substances Data)

Upstream product

• 74853-07-9 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one 
• 890342-21-9 C₈H₈BrN₃O₂ 
• 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 
• 154003-23-3 (2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-4-tozyloxymethyl-1,3-dioxolane 
• 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 
• 214117-52-9 2,4-dihydro-4-(4-bromophenyl)-2-[(2S,3R)-[3-(1,1-dimethylethyl)dimethylsiloxy]-but-2-yl]-3H-1,2,4-triazol-3-one 
• 648416-96-0 2,4-dihydro-4-(4-bromophenyl)-2-[(2S,3R)-(3-hydroxy-2-butyl)]-3H-1,2,4-triazol-3-one 
• 214117-50-7 2,4-dihydro-4-(4-bromophenyl)-3H-1,2,4-triazol-3-one 
• 67914-60-7 N-acetyl-N'-(4-hydroxyphenyl)piperazine 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 2493-02-9 4-bromophenyl isocyanate 

Relevant articles and documents

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).

Efficient stereoselective synthesis of cis, syn-hydroxyitraconazole isomers

The first stereoselective synthesis of cis, syn-hydroxyitraconazole isomers via a tricomponent coupling strategy is described. The isomers are prepared from two chiral subunits and connected via an achiral linker. A highly stereoselective route to the cis,syn-isomers is presented.