138511-90-7

Basic information

• Product Name: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate
• Synonyms: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate
• CAS NO: 138511-90-7
• Molecular Weight: 278.277
• Mol File: 138511-90-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate(138511-90-7)
• EPA Substance Registry System: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] methanesulfonate(138511-90-7)

Safety Data

• Hazardous Substances Data: 138511-90-7(Hazardous Substances Data)

Upstream product

• 127001-03-0 (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 126918-15-8 (S)-2-(p-toluenesulfonyloxy)-2',4'-difluoropropiophenone 
• 138373-68-9 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanyl-butan-2-ol 
• 743449-16-3 1-[(1S)-2-(2,4-difluorophenyl)-1-methylprop-2-enyloxy]-1,1-dimethyl-1-silaethane 
• 743449-15-2 (2S)-1-(2,4-difluorophenyl)-2-(1,1-dimethyl-1-silaethoxy)-propan-1-one 
• 126918-32-9 (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol 
• 126918-33-0 (1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 124-63-0 methanesulfonyl chloride 
• 126918-18-1 (2S^*,3R^*)-2-(2,4-Difluorophenyl)-1-(dimethylisopropoxysilyl)-3-(tetrahydropyran-2-yloxy)-2-butanol 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 126918-21-6 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol 

Downstream Products

• 377078-86-9 1-(2,2-diethoxyethyl)-1-[(1S,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]urea 
• 377078-89-2 1-[(1S,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-(1H,3H)-imidazolone 
• 377078-83-6 (2R,3S)-3-(2,2-diethoxyethyl)amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 

Relevant articles and documents

Optically active antifungal azoles: Synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

A series of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]- ethyl}-tetrazol-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12μg/mL for C. albicans, C. albicans V-01-191A-261 (resistant strain); 0.25μg/mL for C. tropicalis, C. parapsilosis ATCC 22019 and C. krusei and MIC value of 0.5μg/mL for C. glabrata, C. krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5μg/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25μg/mL) against C. neoformans.

Triazole antifungals. III. Stereocontrolled synthesis of an optically active triazolylmethyloxirane precursor to antifungal oxazolidine derivatives

Stereocontrolled synthesis of an optically active triazolylmethyloxirane 2, an important intermediate for the preparation of antifungal oxazolidine compounds 1, was achieved by two methods using L-lactic acid as a starting material. The key intermediate ketone 6 used in the procedures also served for the synthesis of the enantiomer of 2 and the corresponding diastereomeric epoxide.