(2S)-2-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}propanoic acid

• ChemBase ID: 68612
• Molecular Formular: C16H22N2O6
• Molecular Mass: 338.35568
• Monoisotopic Mass: 338.14778643
• SMILES: C(=O)([C@H](CNC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)CNC(=O)OC(C)(C)C)OCc1ccccc1
• InChI: InChI=1S/C16H22N2O6/c1-16(2,3)24-14(21)17-9-12(13(19)20)18-15(22)23-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,18,22)(H,19,20)/t12-/m0/s1
• InChIKey: WJKGPJRAGHSOLM-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{[(tert-butoxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoic acid
• Synonyms: (S)-2-N-Cbz-3-N-Boc-propanoic acid; Nα-Z-Nβ-Boc-L-2,3-diaminopropionic acid; Z-3-(Boc-amino)-L-alanine; Z-Dap(Boc)-OH; Nα-Z-Nβ-Boc-L-2,3-二氨基丙酸; Z-3-(Boc-氨基)-L-丙氨酸

Database IDs

• CAS Number: 16947-84-5
• MDL Number: MFCD00237342
• Beilstein Number: 3629152
• PubChem SID: 24890197; 162034342
• PubChem CID: 2756240

CALCULATED PROPERTIES

• Acid pKa: 3.7620308
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.18333094
• LogD (pH = 7.4): -1.3572036
• Log P: 1.9222052
• Molar Refractivity: 84.2515 cm^3
• Polarizability: 33.165592 Å^3
• Polar Surface Area: 113.96 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -12.0±1°, c = 1% in methanol

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 95+%
• Empirical Formula (Hill Notation): C16H22N2O6

DETAILS

Sigma Aldrich - 95732

Packaging
500 mg in poly tube