(2S)-5-[({[(benzyloxy)carbonyl]amino}({[(benzyloxy)carbonyl]imino})methyl)amino]-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

• ChemBase ID: 152339
• Molecular Formular: C27H34N4O8
• Molecular Mass: 542.58086
• Monoisotopic Mass: 542.23766407
• SMILES: CC(C)(C)OC(=O)N[C@@H](CCCN/C(=N/C(=O)OCc1ccccc1)/NC(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(N/C(=N\C(=O)OCc1ccccc1)/NCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C)OCc1ccccc1
• InChI: InChI=1S/C27H34N4O8/c1-27(2,3)39-26(36)29-21(22(32)33)15-10-16-28-23(30-24(34)37-17-19-11-6-4-7-12-19)31-25(35)38-18-20-13-8-5-9-14-20/h4-9,11-14,21H,10,15-18H2,1-3H3,(H,29,36)(H,32,33)(H2,28,30,31,34,35)/t21-/m0/s1
• InChIKey: ZWRJPLNCTNRXPE-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-[({[(benzyloxy)carbonyl]amino}({[(benzyloxy)carbonyl]imino})methyl)amino]-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid
• IUPAC Traditional name: (2S)-5-[({[(benzyloxy)carbonyl]amino}({[(benzyloxy)carbonyl]imino})methyl)amino]-2-[(tert-butoxycarbonyl)amino]pentanoic acid
• Synonyms: Nα-Boc-Nδ,Nω-di-Z-L-arginine; Boc-Arg(Z)2-OH; Nα-Boc-Nδ,Nω-二苄氧羰基-L-精氨酸

Database IDs

• CAS Number: 51219-19-3
• MDL Number: MFCD00236824
• Beilstein Number: 4914609
• PubChem SID: 162246484; 24849314
• PubChem CID: 11731272

CALCULATED PROPERTIES

• Acid pKa: 3.4945474
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.1615663
• LogD (pH = 7.4): 0.780287
• Log P: 4.1586213
• Molar Refractivity: 139.6633 cm^3
• Polarizability: 54.584747 Å^3
• Polar Surface Area: 164.65 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ~140 °C (dec.)
• Optical Rotation: [α]20/D +2.5±0.5°, c = 1% in methanol

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C27H34N4O8

DETAILS

Sigma Aldrich - 15493

Packaging
2.5 g in glass bottle