benzyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}propanoate

• ChemBase ID: 165399
• Molecular Formular: C23H28N2O6
• Molecular Mass: 428.47822
• Monoisotopic Mass: 428.19473663
• SMILES: C(OC(=O)[C@H](CNC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1)c1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)OCc1ccccc1)CNC(=O)OC(C)(C)C)OCc1ccccc1
• InChI: InChI=1S/C23H28N2O6/c1-23(2,3)31-21(27)24-14-19(20(26)29-15-17-10-6-4-7-11-17)25-22(28)30-16-18-12-8-5-9-13-18/h4-13,19H,14-16H2,1-3H3,(H,24,27)(H,25,28)/t19-/m0/s1
• InChIKey: PKJSHTUXTOKIBY-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}propanoate
• IUPAC Traditional name: benzyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate
• Synonyms: 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-N-[(phenylmethoxy)carbonyl]-L-Alanine Phenylmethyl Ester; Z-L-Dap(Boc)-Obn

Database IDs

• CAS Number: 239785-37-6
• PubChem SID: 162259532
• PubChem CID: 71315181

CALCULATED PROPERTIES

• Acid pKa: 13.242928
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7925723
• LogD (pH = 7.4): 3.7925718
• Log P: 3.7925723
• Molar Refractivity: 113.6332 cm^3
• Polarizability: 44.766975 Å^3
• Polar Surface Area: 102.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D185400

Used in the preparation of N-hydroxybenzamidine derivatives of β-amino-L-alanine with potent affinity to receptor of cell adhesion activating protein.