(2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoic acid

• ChemBase ID: 152700
• Molecular Formular: C12H16N2O4
• Molecular Mass: 252.26644
• Monoisotopic Mass: 252.111007
• SMILES: c1ccc(cc1)COC(=O)N[C@@H](CCN)C(=O)O
• Canonical SMILES: NCC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C12H16N2O4/c13-7-6-10(11(15)16)14-12(17)18-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,14,17)(H,15,16)/t10-/m0/s1
• InChIKey: KXMSCBRTBLPGIN-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoic acid
• IUPAC Traditional name: (2S)-4-amino-2-{[(benzyloxy)carbonyl]amino}butanoic acid
• Synonyms: Z-Dbu-OH; Nα-Z-L-2,4-diaminobutyric acid; Z-Dab-OH; N-α-苄氧羰基-L-2,4-二氨基丁酸

Database IDs

• CAS Number: 62234-40-6
• MDL Number: MFCD00077904
• Beilstein Number: 2288043
• PubChem SID: 162246843; 24890254
• PubChem CID: 7018863

CALCULATED PROPERTIES

• Acid pKa: 3.5178242
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.7762268
• LogD (pH = 7.4): -1.7742691
• Log P: -1.773287
• Molar Refractivity: 64.2439 cm^3
• Polarizability: 25.360088 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 194-196 °C
• Optical Rotation: [α]20/D -9.5±0.5°, c = 1% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, TLC)
• Empirical Formula (Hill Notation): C12H16N2O4

DETAILS

Sigma Aldrich - 96083

Other Notes
Mono-protected derivative of L-2,4-diaminobutyric acid; used e.g. for the synthesis of α-amino-γ-guanidino butyric acid1,2; synthesis of an analog of virginiamycin3
Packaging
1 g in glass bottle