(2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-(2-phenylethyl)oct-6-yne-1,3-dione

• ChemBase ID: 162403
• Molecular Formular: C48H48N2O5
• Molecular Mass: 732.90512
• Monoisotopic Mass: 732.35632265
• SMILES: c1ccccc1CCC(CC(=O)[C@@H](C(=O)N1C(=O)OC[C@H]1c1ccccc1)[C@@H](c1cccc(c1)N(Cc1ccccc1)Cc1ccccc1)CC)(O)C#CC
• Canonical SMILES: CC#CC(CC(=O)[C@@H](C(=O)N1C(=O)OC[C@H]1c1ccccc1)[C@@H](c1cccc(c1)N(Cc1ccccc1)Cc1ccccc1)CC)(CCc1ccccc1)O
• InChI: InChI=1S/C48H48N2O5/c1-3-29-48(54,30-28-36-18-9-5-10-19-36)32-44(51)45(46(52)50-43(35-55-47(50)53)39-24-15-8-16-25-39)42(4-2)40-26-17-27-41(31-40)49(33-37-20-11-6-12-21-37)34-38-22-13-7-14-23-38/h5-27,31,42-43,45,54H,4,28,30,32-35H2,1-2H3/t42-,43+,45+,48-/m1/s1
• InChIKey: NWQXDMCBNUXVPH-OOYLSIGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-(2-phenylethyl)oct-6-yne-1,3-dione
• IUPAC Traditional name: (2S,5R)-2-[(1S)-1-[3-(dibenzylamino)phenyl]propyl]-5-hydroxy-1-[(4R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-(2-phenylethyl)oct-6-yne-1,3-dione
• Synonyms: [4R-[3[2S*(S*),5R*],4R*]]- 3-[2-[1-[3-[Bis(phenylmethyl)amino]phenyl]propyl]-5-hydroxy-1,3-dioxo-5-(2-phenylethyl)-6-octynyl]-4-phenyl-2-oxazolidinone; [4R-[3(2(S*),5(R*),4R]]-3-[2-[1-[3-[Bis(phenylmethyl)amino]phenyl]propyl]-5-hydroxy-1,3-dioxo-5-(2-phenylethyl)-6-octynyl]-4-phenyl-2-oxazolidinone

Database IDs

• CAS Number: 188559-22-0
• PubChem SID: 162256538
• PubChem CID: 10974638

CALCULATED PROPERTIES

• Acid pKa: 13.072354
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 10.970452
• LogD (pH = 7.4): 10.971298
• Log P: 10.97131
• Molar Refractivity: 217.846 cm^3
• Polarizability: 83.77878 Å^3
• Polar Surface Area: 87.15 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - B522100

Intermediate for the synthesis of Tipranavir.

REFERENCES

• Judge, T. M., et al.: J. Am. Chem. Soc., 119, 3627 (1997).