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Usage

Uses

Used in Pharmaceutical Synthesis:
cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-ylmethyl benzoate is used as an intermediate in the synthesis of trans-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol (D431560), which is an impurity of Ketoconazole (K186000). This application is significant in the pharmaceutical industry for the development and production of antifungal medications.
Used in Antifungal Treatments:
In the pharmaceutical industry, cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-ylmethyl benzoate contributes to the synthesis of Ketoconazole, a widely used antifungal agent. It is effective against a broad range of fungal infections, including those caused by yeasts, dermatophytes, and dimorphic fungi, making it a valuable compound in the development of antifungal medications.

InChI:InChI=1/C21H18Cl2N2O4/c22-16-6-7-18(19(23)10-16)21(13-25-9-8-24-14-25)28-12-17(29-21)11-27-20(26)15-4-2-1-3-5-15/h1-10,14,17H,11-13H2

Upstream product

• 288-32-4 1H-imidazole 
• 170210-39-6 (2R,4R)-(+)-<2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl>methyl benzoate 
• 532-32-1 sodium benzoate 
• 331949-30-5 2-bromomethyl-2-(2,4-dichlorophenyl)-4-phenylcarbonyloxymethyl-1,3-dioxolane 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 61397-56-6 (+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate 
• 172032-21-2 (2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methanol 
• 68751-57-5 2-(2,4-dichlorophenyl)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane 

Downstream Products

• 61397-58-8 cis-2-(2,4-Dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane-4-methanol 
• 85650-50-6 cis-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl toluene-p-sulphonate 
• 65277-42-1 ketoconazole 
• 134071-44-6 [cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl] 4-methyl-benzenesulfonate 
• 170210-42-1 (2R,4S)-(+)-2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolane-4-methanol 

Relevant academic research and scientific papers

Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)- 1,3-dioxolanes

A series of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1,3-dioxolanes Ia-u was synthesized and tested in vitro against pathogenic fungi in man, animals and plants: Candida albicans, Aspergillus flavus and Fusarium solani. Compounds Iq-t with two polyazol groups have an in vitro activity against these fungi with MIC (minimum inhibitory concentration) value of 5 μg mL-1.

Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin

Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)- or (S)-epichlorohydrin has been developed.The key-step of syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-14a and (2R,4R)-15a or of their enentiomers, followed by crystalization of the corresponding cis-benzoates, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1.The ee's of (+)- and (-)-ketocanazole were determined by HPLC on the CSP Chiracel OD-H.

Synthesis and 13C NMR Spectra of cis- and trans-methyl>>-1,3-dioxolane-4-methanols

Syntheses and 13C nmr spectra of a number of cis and trans 2-(haloaryl)-2--4-(hydroxymethyl)-1,3-dioxolanes are described.The haloaryl groups are 2,4-dichloro, 2,4-difluoro-, 4-chloro- and 4-bromophenyl.In these series, some of the cis compounds become available through crystalline bromo benzoates 5.Separations of some trans isomers are achieved through fractional crystallizations of imidazolyl benzoate nitrates 6.Stereochemical assignments are based primarily on one major 13C chemical shift difference, namely that of C-4 of the 1,3-dioxolane ring, the chemical shift of the trans isomers being 1.0-2.5 ppm downfield from that of the cis isomers.