(3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid

• ChemBase ID: 144449
• Molecular Formular: C13H23NO6
• Molecular Mass: 289.32482
• Monoisotopic Mass: 289.15253746
• SMILES: CC(C)(C)OC(=O)[C@H](CC(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: OC(=O)C[C@@H](C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C13H23NO6/c1-12(2,3)19-10(17)8(7-9(15)16)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,15,16)/t8-/m0/s1
• InChIKey: RAUQRYTYJIYLTF-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-4-(tert-butoxy)-3-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid
• IUPAC Traditional name: (3S)-4-(tert-butoxy)-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid
• Synonyms: N-[(1,1-Dimethylethoxy)carbonyl]-L-aspartic Acid 1-(1,1-Dimethylethyl) Ester; N-α-t-Boc-L-aspartic Acid α-tert-Butyl Ester; N-(tert-Butoxycarbonyl)aspartic Acid α-tert-Butyl Ester; BOC-ASP-OTBU; N-tert-Boc-L-aspartic Acid tert-Butyl Ester; α-tert-Butyl-N-Boc-L-aspartate; Boc-Asp-OtBu; Boc-ASP-OtBu

Database IDs

• CAS Number: 34582-32-6
• MDL Number: MFCD00038272
• Beilstein Number: 4191701
• PubChem SID: 162238664
• PubChem CID: 7010517

CALCULATED PROPERTIES

• Acid pKa: 4.3669186
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.30924127
• LogD (pH = 7.4): -1.441854
• Log P: 1.4714279
• Molar Refractivity: 69.9804 cm^3
• Polarizability: 27.997587 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate; Methanol
• Apperance: White solid
• Melting Point: 101-103°C
• Optical Rotation: [α]/D -24.5±1.5°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (TLC); 95+%
• Compostion: carbon content, 53.0-55.0%; nitrogen content, 4.5-5.1%
• Empirical Formula (Hill Notation): C13H23NO6

DETAILS

Toronto Research Chemicals - B621300

An aspartic acid derivative used in stereoselective synthesis; a potent, selective proteasome inhibitor.

REFERENCES

• Elofsson, M., et al.: Chem. Biol., 6, 811 (1999)
• Myung, J., et al.: Mol. Cell., 7, 411 (1999)
• Fukatsu, K., et al.: J. Med. Chem., 45, 4212 (1999)