3-[(4S)-3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl]propanoic acid

• ChemBase ID: 145659
• Molecular Formular: C14H15NO6
• Molecular Mass: 293.272
• Monoisotopic Mass: 293.08993721
• SMILES: c1ccc(cc1)COC(=O)N1COC(=O)[C@@H]1CCC(=O)O
• Canonical SMILES: O=C(N1COC(=O)[C@@H]1CCC(=O)O)OCc1ccccc1
• InChI: InChI=1S/C14H15NO6/c16-12(17)7-6-11-13(18)21-9-15(11)14(19)20-8-10-4-2-1-3-5-10/h1-5,11H,6-9H2,(H,16,17)/t11-/m0/s1
• InChIKey: AYOCGDFDOZVEKT-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4S)-3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl]propanoic acid
• IUPAC Traditional name: 3-[(4S)-3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl]propanoic acid
• Synonyms: (S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionic acid; (4S)-5-Oxo-3-[(phenylmethoxy)carbonyl]-4-oxazolidinepropanoic Acid; (S)-3-Benzyloxycarbonyl-5-oxo-4-oxazolidinepropanoic Acid; (S)-(+)-3-(苄氧羰基)-5-氧代-4-噁唑烷丙酸

Database IDs

• CAS Number: 23632-67-9
• MDL Number: MFCD00799475
• PubChem SID: 24866901; 162239863
• PubChem CID: 688249

CALCULATED PROPERTIES

• Acid pKa: 3.7597675
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.20216596
• LogD (pH = 7.4): -1.7415028
• Log P: 1.538895
• Molar Refractivity: 69.474 cm^3
• Polarizability: 27.64865 Å^3
• Polar Surface Area: 93.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Clear Colorless Oil
• Flash Point: 113 °C; 235.4 °F
• Density: 1.05 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.535(lit.)
• Optical Rotation: [α]22/D +88°, c = 1 in methanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C14H15NO6

DETAILS

Sigma Aldrich - 429929

Packaging
1 g in glass bottle

REFERENCES

• Esslinger, C., et al.: Bioorg. Med. Chem., 13, 1111 (2005)
• Alexander, J., et al.: Biochem., 47, 1228 (2005)