(2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

• ChemBase ID: 179562
• Molecular Formular: C16H14F3N5O
• Molecular Mass: 349.3104696
• Monoisotopic Mass: 349.11504475
• SMILES: C(C([C@@H](c1ncncc1F)C)(c1c(cc(cc1)F)F)O)n1cncn1
• Canonical SMILES: Fc1ccc(c(c1)F)C([C@@H](c1ncncc1F)C)(Cn1cncn1)O
• InChI: InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m1/s1
• InChIKey: BCEHBSKCWLPMDN-HWPZZCPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
• IUPAC Traditional name: (2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
• Synonyms: (αS,βR)-α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol; [S-(R*,S*)]-α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol; ent-Voriconazole

Database IDs

• CAS Number: 137234-63-0
• PubChem SID: 164235472
• PubChem CID: 15230631

CALCULATED PROPERTIES

• Acid pKa: 12.708208
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8227984
• LogD (pH = 7.4): 1.8230275
• Log P: 1.8230326
• Molar Refractivity: 95.278 cm^3
• Polarizability: 30.730742 Å^3
• Polar Surface Area: 76.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 130-132°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V760005

The (2S,3R) enantiomer in Voriconazole (V760000) drug substance.

REFERENCES

• Gage, R., et al.: J. Pharm. Biomed. Anal., 17, 1449 (1998)
• Owens, P., et al.: Enantiomer, 4, 79 (1998)
• Pehourcq, F., et al.: Biomed. Chromatogr., 18, 719 (1998)
• Sellers, J., et al.: J. Pharm. Biomed. Anal., 41, 1088 (1998)