tert-butyl N-[(2S,3S)-4-({[(tert-butoxy)carbonyl]amino}({[4-(pyridin-2-yl)phenyl]methyl})amino)-3-hydroxy-1-(2H5)phenylbutan-2-yl]carbamate

• ChemBase ID: 166348
• Molecular Formular: C32H42N4O5
• Molecular Mass: 562.69968
• Monoisotopic Mass: 562.31552046
• SMILES: c1(C[C@@H]([C@H](CN(Cc2ccc(cc2)c2ccccn2)NC(=O)OC(C)(C)C)O)NC(=O)OC(C)(C)C)ccccc1
• Canonical SMILES: O=C(OC(C)(C)C)NN(C[C@@H]([C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1)O)Cc1ccc(cc1)c1ccccn1
• InChI: InChI=1S/C32H42N4O5/c1-31(2,3)40-29(38)34-27(20-23-12-8-7-9-13-23)28(37)22-36(35-30(39)41-32(4,5)6)21-24-15-17-25(18-16-24)26-14-10-11-19-33-26/h7-19,27-28,37H,20-22H2,1-6H3,(H,34,38)(H,35,39)/t27-,28-/m0/s1
• InChIKey: KYSDBVSJLBOZDZ-NSOVKSMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3S)-4-({[(tert-butoxy)carbonyl]amino}({[4-(pyridin-2-yl)phenyl]methyl})amino)-3-hydroxy-1-(^2H₅)phenylbutan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3S)-4-{[(tert-butoxycarbonyl)amino]({[4-(pyridin-2-yl)phenyl]methyl})amino}-3-hydroxy-1-(^2H₅)phenylbutan-2-yl]carbamate
• Synonyms: 2-[(2S,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-4-phenyl-d5-butyl]-2-[[4-(2-pyridinyl)phenyl]methyl]hydrazinecarboxylic Acid 1,1-Dimethylethyl Ester; Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir-d5

Database IDs

• PubChem SID: 162260481
• PubChem CID: 46781143

CALCULATED PROPERTIES

• Log P: 5.189813
• Molar Refractivity: 158.0315 cm^3
• Polarizability: 63.463833 Å^3
• Polar Surface Area: 113.02 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false
• Acid pKa: 12.404871
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 5.15607
• LogD (pH = 7.4): 5.189367

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D290332

An intermediate for the synthesis of Atazanavir-d5 and the preparation of some peptide analogs.

REFERENCES

• Martin, J., et al.: Prog. Med. Chem., 32, 239 (1995)
• Jadhav, P., et al.: J. Med. Chem., 40, 181 (1995)
• Bold, G., et al.: J. Med. Chem., 41, 3387 (1998).