(2S)-2-{[(tert-butoxy)carbonyl]amino}-5-[3-(4-methylbenzenesulfonyl)carbamimidamido]pentanoic acid

• ChemBase ID: 38399
• Molecular Formular: C18H28N4O6S
• Molecular Mass: 428.50312
• Monoisotopic Mass: 428.17295564
• SMILES: N(C(=N)NCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: N=C(NS(=O)(=O)c1ccc(cc1)C)NCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C18H28N4O6S/c1-12-7-9-13(10-8-12)29(26,27)22-16(19)20-11-5-6-14(15(23)24)21-17(25)28-18(2,3)4/h7-10,14H,5-6,11H2,1-4H3,(H,21,25)(H,23,24)(H3,19,20,22)/t14-/m0/s1
• InChIKey: WBIIPXYJAMICNU-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-5-[3-(4-methylbenzenesulfonyl)carbamimidamido]pentanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-5-[3-(4-methylbenzenesulfonyl)carbamimidamido]pentanoic acid
• Synonyms: Nα-Boc-Nω-tosyl-L-arginine; Boc-Arg(Tos)-OH; Boc-Arg(Tos)-OH; Nα-Boc-Nω-对甲苯磺酰基-L-精氨酸

Database IDs

• CAS Number: 13836-37-8
• EC Number: 237-549-2
• MDL Number: MFCD00065557
• Beilstein Number: 2683538
• PubChem SID: 24849333; 161001706
• PubChem CID: 83767

CALCULATED PROPERTIES

• Acid pKa: 3.3989496
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.295977
• LogD (pH = 7.4): -1.0074842
• Log P: 0.41540962
• Molar Refractivity: 117.0311 cm^3
• Polarizability: 42.03841 Å^3
• Polar Surface Area: 157.68 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~90 °C (dec.)
• Optical Rotation: [α]20/D -3.5±0.5°, c = 4% in DMF

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

• Impurities: ~2% water
• Empirical Formula (Hill Notation): C18H28N4O6S

DETAILS

Sigma Aldrich - 15506

General description
crystallized with ~10% (w/w) ethyl acetate
Packaging
5 g in glass bottle