tert-butyl N-[(2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 166863
• Molecular Formular: C37H44N2O3
• Molecular Mass: 564.75686
• Monoisotopic Mass: 564.33519328
• SMILES: [C@@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O)(Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H](C[C@@H]([C@@H](N(Cc1ccccc1)Cc1ccccc1)Cc1ccccc1)O)Cc1ccccc1
• InChI: InChI=1S/C37H44N2O3/c1-37(2,3)42-36(41)38-33(24-29-16-8-4-9-17-29)26-35(40)34(25-30-18-10-5-11-19-30)39(27-31-20-12-6-13-21-31)28-32-22-14-7-15-23-32/h4-23,33-35,40H,24-28H2,1-3H3,(H,38,41)/t33-,34-,35-/m0/s1
• InChIKey: FEAVBRDFTRUZPF-IMKBVMFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: [(1S,3S,4S)-4-[Bis(phenylmethyl)amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic Acid 1,1-Dimethylethyl Ester; (2S,3S,5S)-2-(N,N-Dibenzylamino)-3-hydroxy-5-(tert-butyloxycarbonylamino)-1,6-diphenylhexane

Database IDs

• CAS Number: 162849-93-6
• PubChem SID: 162260996
• PubChem CID: 15383368

CALCULATED PROPERTIES

• Acid pKa: 14.415391
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.599014
• LogD (pH = 7.4): 6.053855
• Log P: 7.909657
• Molar Refractivity: 170.9396 cm^3
• Polarizability: 67.08623 Å^3
• Polar Surface Area: 61.8 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 40-42°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D416954

(2S,3S,5S)-2-(N,N-Dibenzylamino)-3-hydroxy-5-(tert-butyloxycarbonylamino)-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)