(2S,3S)-3-amino-4-phenyl-1-(1-{[4-(pyridin-2-yl)phenyl]methyl}hydrazin-1-yl)butan-2-ol; methane

• ChemBase ID: 166345
• Molecular Formular: C23H30N4O
• Molecular Mass: 378.5105
• Monoisotopic Mass: 378.2419616
• SMILES: c1(C[C@@H]([C@H](CN(Cc2ccc(cc2)c2ccccn2)N)O)N)ccccc1.C
• Canonical SMILES: NN(C[C@@H]([C@H](Cc1ccccc1)N)O)Cc1ccc(cc1)c1ccccn1.C
• InChI: InChI=1S/C22H26N4O.CH4/c23-20(14-17-6-2-1-3-7-17)22(27)16-26(24)15-18-9-11-19(12-10-18)21-8-4-5-13-25-21;/h1-13,20,22,27H,14-16,23-24H2;1H4/t20-,22-;/m0./s1
• InChIKey: FBFQCJNRUJQYFJ-DTRWSJPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-3-amino-4-phenyl-1-(1-{[4-(pyridin-2-yl)phenyl]methyl}hydrazin-1-yl)butan-2-ol; methane
• IUPAC Traditional name: (2S,3S)-3-amino-4-phenyl-1-(1-{[4-(pyridin-2-yl)phenyl]methyl}hydrazin-1-yl)butan-2-ol; methane
• Synonyms: (αS,βS)-β-Amino-α-[[1-[[4-(2-pyridinyl)phenyl]methyl]hydrazino]methyl]benzenepropanol Trihydrochloride; [S-(R*,R*)]-β-Amino-α-[[1-[[4-(2-pyridinyl)phenyl]methyl]hydrazino]methyl]benzenepropanol Trihydrochloride; Des-N-(methoxycarbonyl)-L-tert-leucine Atazanavir Trihydrochloride

Database IDs

• CAS Number: 198904-87-9
• PubChem SID: 162260478
• PubChem CID: 71315699

CALCULATED PROPERTIES

• Acid pKa: 14.181887
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.8998569
• LogD (pH = 7.4): 0.33277678
• Log P: 2.3174388
• Molar Refractivity: 109.3475 cm^3
• Polarizability: 44.195236 Å^3
• Polar Surface Area: 88.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Light Yellow Oil

DETAILS

Toronto Research Chemicals - D290320

An intermediate for the synthesis of Atazanavir and the preparation of some peptide analogs.

REFERENCES

• Martin, J., et al.: Prog. Med. Chem., 32, 239 (1995)
• Bold, G., et al.: J. Med. Chem., 41, 3387 (1998).