(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(cyclohexyloxy)-4-oxobutanoic acid

• ChemBase ID: 38419
• Molecular Formular: C15H25NO6
• Molecular Mass: 315.3621
• Monoisotopic Mass: 315.16818753
• SMILES: C(=O)(C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)OC1CCCCC1
• Canonical SMILES: O=C(OC1CCCCC1)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C15H25NO6/c1-15(2,3)22-14(20)16-11(13(18)19)9-12(17)21-10-7-5-4-6-8-10/h10-11H,4-9H2,1-3H3,(H,16,20)(H,18,19)/t11-/m0/s1
• InChIKey: NLPQIWFEEKQBBN-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(cyclohexyloxy)-4-oxobutanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-4-(cyclohexyloxy)-4-oxobutanoic acid
• Synonyms: Boc-L-aspartic acid 4-cyclohexyl ester; Boc-Asp(OcHex)-OH; N-Alpha-t-Boc-L-aspartic acid beta-cyclohexyl ester; N-t-BOC-L-ASPARTIC ACID β-CYCLOHEXYL ESTER; Boc-Asp(OcHx)-OH; Boc-L-天冬氨酸-4-环己酯

Database IDs

• CAS Number: 73821-95-1
• MDL Number: MFCD00061996
• Beilstein Number: 3563576
• PubChem SID: 24849395; 161001726
• PubChem CID: 7009416

CALCULATED PROPERTIES

• Acid pKa: 3.9146597
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.62517047
• LogD (pH = 7.4): -0.98921704
• Log P: 2.2167387
• Molar Refractivity: 77.189 cm^3
• Polarizability: 30.936178 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 93-95 °C
• Optical Rotation: [α]20/D -21.0±1.5°, c = 2% 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

• Purity: ≥98.0% (T); 95+%
• Linear Formula: C6H11OCOCH2CH(COOH)NHCOOC(CH3)3

DETAILS

MP Biomedicals - 02199057

Reduces aspartimide formation, particularly in Asp-Gly sequences.

Sigma Aldrich - 15398

Packaging
5 g in glass bottle

REFERENCES

• J.P. Tam, et al. Tetrahedron Lett., 42: 4033, (1979)
• E. Nicolas, et al. Tetrahedron Lett., 30: 497, (1989)
• B. Penke, G. Jung and E. Bayer (Eds.): Peptides 1988, Walter de Gruyer & Company.