[(3S,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 178715
• Molecular Formular: C21H21F2N3O4S
• Molecular Mass: 449.4709464
• Monoisotopic Mass: 449.12208361
• SMILES: c1c(ccc(c1F)[C@]1(C[C@@H](CO1)COS(=O)(=O)c1ccc(cc1)C)Cn1cncn1)F
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H]1CO[C@@](C1)(Cn1ncnc1)c1ccc(cc1F)F
• InChI: InChI=1S/C21H21F2N3O4S/c1-15-2-5-18(6-3-15)31(27,28)30-11-16-9-21(29-10-16,12-26-14-24-13-25-26)19-7-4-17(22)8-20(19)23/h2-8,13-14,16H,9-12H2,1H3/t16-,21-/m0/s1
• InChIKey: DFWVLCJRFGIRAK-KKSFZXQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(3S,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol; (5R-cis)-Toluene-4-sulfonic Acid 5-(2,4-Difluorophenyl)-5-[1,2,4]triazol-1-ylmethyltetrahydrofuran-3-ylmethyl Ester

Database IDs

• CAS Number: 149809-43-8
• PubChem SID: 164234625
• PubChem CID: 10895629

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.600553
• LogD (pH = 7.4): 3.6007807
• Log P: 3.6007836
• Molar Refractivity: 121.5694 cm^3
• Polarizability: 42.44554 Å^3
• Polar Surface Area: 83.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Crystalline Solid
• Melting Point: 100-102°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T535900

Posaconazole intermediate. Antifungal agent.

REFERENCES

• Ator, M., et al.: J. Med. Chem., 35, 100 (1992)
• Andriole, V., et al.: J. Antimicrob. Chemother., 44, 151 (1992)
• Beuchet, P., et al.: Bioorg. Med. Chem., 9, 1599 (1992)