1-[(2S,3S)-2-(benzyloxy)pentan-3-yl]-4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 161932
• Molecular Formular: C44H48F2N8O4
• Molecular Mass: 790.8999264
• Monoisotopic Mass: 790.3766585
• SMILES: c1c(ccc(c1)n1c(=O)n(nc1)[C@H]([C@@H](OCc1ccccc1)C)CC)N1CCN(CC1)c1ccc(cc1)OC[C@H]1C[C@](OC1)(Cn1ncnc1)c1c(cc(cc1)F)F
• Canonical SMILES: CC[C@H](n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OC[C@@H]1CO[C@@](C1)(Cn1cncn1)c1ccc(cc1F)F)[C@@H](OCc1ccccc1)C
• InChI: InChI=1S/C44H48F2N8O4/c1-3-42(32(2)56-25-33-7-5-4-6-8-33)54-43(55)53(31-49-54)38-12-10-36(11-13-38)50-19-21-51(22-20-50)37-14-16-39(17-15-37)57-26-34-24-44(58-27-34,28-52-30-47-29-48-52)40-18-9-35(45)23-41(40)46/h4-18,23,29-32,34,42H,3,19-22,24-28H2,1-2H3/t32-,34+,42-,44-/m0/s1
• InChIKey: XZBSQKGAKKWACB-QCKBNUSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,3S)-2-(benzyloxy)pentan-3-yl]-4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 2-[(2S,3S)-2-(benzyloxy)pentan-3-yl]-4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1,2,4-triazol-3-one
• Synonyms: 2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-(phenylmethoxy)propyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol; O-Benzyl Posaconazole

Database IDs

• CAS Number: 170985-86-1
• PubChem SID: 162256067
• PubChem CID: 11136519

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 7.7622805
• LogD (pH = 7.4): 7.7736382
• Log P: 7.7737846
• Molar Refractivity: 230.0696 cm^3
• Polarizability: 82.24671 Å^3
• Polar Surface Area: 100.79 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B288660

Precursor to the fungicide, Posaconazole.

REFERENCES

• Heeres, J., et al.: J. Med. Chem. 27, 894 (1984)
• Wood, P., et al.: Drug Discov. Develop., 1, 34 (1984)