(2S)-2-{[(benzyloxy)carbonyl]amino}-3-carbamoylpropanoic acid

• ChemBase ID: 59659
• Molecular Formular: C12H14N2O5
• Molecular Mass: 266.24996
• Monoisotopic Mass: 266.09027156
• SMILES: C(=O)(N[C@@H](CC(=O)N)C(=O)O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)O)CC(=O)N)OCc1ccccc1
• InChI: InChI=1S/C12H14N2O5/c13-10(15)6-9(11(16)17)14-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,15)(H,14,18)(H,16,17)/t9-/m0/s1
• InChIKey: FUCKRCGERFLLHP-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-carbamoylpropanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-carbamoylpropanoic acid
• Synonyms: N-Cbz-L-Asparagine; (S)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid; CARBOBENZOXY-L-ASPARAGINE; Z-L-Asparagine; Z-Asn-OH; N(alpha)-Cbz-L-asparagine; Z-Asn-OH; N(alpha)-Benzyloxycarbonyl-L-asparagine; N~2~-[(benzyloxy)carbonyl]-L-asparagine; (S)-N-(benzyloxycarbonyl)asparagine; (2S)-2-{[(benzyloxy)carbonyl]amino}-3-carbamoylpropanoic acid; N-苄氧羰基-L-天冬酰胺; N(α)-苄氧羰基-L-天冬氨酸

Database IDs

• CAS Number: 2304-96-3
• EC Number: 218-969-5
• MDL Number: MFCD00008035
• Beilstein Number: 3085452
• PubChem SID: 162064422; 24892863
• PubChem CID: 75314

CALCULATED PROPERTIES

• Acid pKa: 3.6122403
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.7484039
• LogD (pH = 7.4): -3.2035842
• Log P: 0.13514502
• Molar Refractivity: 64.0349 cm^3
• Polarizability: 25.12501 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 162-166°C; 163-165 °C(lit.); 164-166 °C
• Optical Rotation: [α]20/D +6.3±0.5°, c = 2% in acetic acid; [α]20/D +6°, c = 1.6 in acetic acid; +6 (c=2 in acetic acid)
• Hydrophobicity(logP): 0.145

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 是

Product Information

• Purity: ≥99.0% (T); 95%; 97%; 98%; 98+%; 99%
• Grade: purum
• Linear Formula: NH2COCH2CH(NHCOOCH2C6H5)COOH

DETAILS

MP Biomedicals - 05210810

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C6404

Packaging
10 g in glass bottle

REFERENCES

• N-protected asparagines undergo Hofmann rearrangement with Iodosobenzene diacetate, B24531, under mild conditions, to give ?-amino L-alanine derivatives in good yields: J. Org. Chem., 62, 6918 (1997):