(2S,3S,5S)-5-amino-2-(dibenzylamino)-1,6-diphenylhexan-3-ol

• ChemBase ID: 166864
• Molecular Formular: C32H36N2O
• Molecular Mass: 464.64104
• Monoisotopic Mass: 464.28276378
• SMILES: [C@@H]([C@H](C[C@@H](N)Cc1ccccc1)O)(Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1
• Canonical SMILES: N[C@H](C[C@@H]([C@@H](N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1)O)Cc1ccccc1
• InChI: InChI=1S/C32H36N2O/c33-30(21-26-13-5-1-6-14-26)23-32(35)31(22-27-15-7-2-8-16-27)34(24-28-17-9-3-10-18-28)25-29-19-11-4-12-20-29/h1-20,30-32,35H,21-25,33H2/t30-,31-,32-/m0/s1
• InChIKey: SRVJQTROLWUZRB-CPCREDONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5S)-5-amino-2-(dibenzylamino)-1,6-diphenylhexan-3-ol
• IUPAC Traditional name: (2S,3S,5S)-5-amino-2-(dibenzylamino)-1,6-diphenylhexan-3-ol
• Synonyms: (αS,γS)-γ-Amino-α-[(1S)-1-[Bis(phenylmethyl)amino]-2-phenylethyl]benzenebutanol; (2S,3S,5S)-5-Amino-2-(dibenzylamino)-3-hydroxy-1,6-diphenylhexane; (2S,3S,5S)-2-(N,N-Dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Database IDs

• CAS Number: 156732-15-9
• PubChem SID: 162260997
• PubChem CID: 9890651

CALCULATED PROPERTIES

• Acid pKa: 14.533777
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.022353116
• LogD (pH = 7.4): 2.0887477
• Log P: 6.4175596
• Molar Refractivity: 146.0666 cm^3
• Polarizability: 57.513817 Å^3
• Polar Surface Area: 49.49 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Colourless Thick Oil

DETAILS

Toronto Research Chemicals - D416955

(2S,3S,5S)-2-(N,N-Dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane is an intermediate in the synthesis of Lopinavir(L469480) and Ritonavir (R535000).

REFERENCES

• Stoner, E., et al.: Org. Process Res. Develop., 4, 264 (2000)