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

• ChemBase ID: 173379
• Molecular Formular: C17H24N2O6
• Molecular Mass: 352.38226
• Monoisotopic Mass: 352.1634365
• SMILES: N(C[C@@H](C(=O)OC)NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C
• Canonical SMILES: COC(=O)[C@@H](NC(=O)OCc1ccccc1)CNC(=O)OC(C)(C)C
• InChI: InChI=1S/C17H24N2O6/c1-17(2,3)25-15(21)18-10-13(14(20)23-4)19-16(22)24-11-12-8-6-5-7-9-12/h5-9,13H,10-11H2,1-4H3,(H,18,21)(H,19,22)/t13-/m0/s1
• InChIKey: MDMZRMHNXPKKND-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate
• Synonyms: 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-N-[(phenylmethoxy)carbonyl]-L-alanine Methyl Ester; Methyl 2-(S)-[N-[(Benzyloxy)carbonyl]amino-3-[N-[t-butyloxycarbonyl)amino]-propionate; Methyl 2-(S)-[N-Carbobenzyloxy]amino-3-[N-tert-butyloxycarbonyl]aminopropionate

Database IDs

• CAS Number: 58457-98-0
• PubChem SID: 164229289
• PubChem CID: 10831821

CALCULATED PROPERTIES

• Acid pKa: 13.186746
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.0680993
• LogD (pH = 7.4): 2.0680985
• Log P: 2.0680993
• Molar Refractivity: 89.0206 cm^3
• Polarizability: 35.23453 Å^3
• Polar Surface Area: 102.96 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Tetrahydrofuran
• Apperance: White Solid
• Melting Point: 84-86°C; 85-87°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M294440

Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.

REFERENCES

• Mendre, C., et al.: Tetrahedron Lett., 35, 5429 (1994)
• Shinagaga, S., et al.: J. Med. Chem., 30, 1458 (1994)