ethyl (2R,3S)-2-amino-3-hydroxy-3-(4-methanesulfonylphenyl)propanoate

• ChemBase ID: 174167
• Molecular Formular: C12H17NO5S
• Molecular Mass: 287.33208
• Monoisotopic Mass: 287.08274365
• SMILES: c1cc(ccc1[C@@H]([C@H](C(=O)OCC)N)O)S(=O)(=O)C
• Canonical SMILES: CCOC(=O)[C@@H]([C@H](c1ccc(cc1)S(=O)(=O)C)O)N
• InChI: InChI=1S/C12H17NO5S/c1-3-18-12(15)10(13)11(14)8-4-6-9(7-5-8)19(2,16)17/h4-7,10-11,14H,3,13H2,1-2H3/t10-,11+/m1/s1
• InChIKey: CEEHCOWSYFANRT-MNOVXSKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,3S)-2-amino-3-hydroxy-3-(4-methanesulfonylphenyl)propanoate
• IUPAC Traditional name: ethyl (2R,3S)-2-amino-3-hydroxy-3-(4-methanesulfonylphenyl)propanoate
• Synonyms: (βS)-β-Hydroxy-4-(methylsulfonyl)-D-phenylalanine Ethyl Ester; D-threo-β-Methylsulfonylphenylserine Ethyl Ester; D-p-Methyl Sulfone Phenyl Ethyl Serinate

Database IDs

• CAS Number: 36983-12-7
• PubChem SID: 164230077
• PubChem CID: 11833038

CALCULATED PROPERTIES

• Acid pKa: 13.459954
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0821682
• LogD (pH = 7.4): -0.51364166
• Log P: -0.49837053
• Molar Refractivity: 69.8451 cm^3
• Polarizability: 28.486406 Å^3
• Polar Surface Area: 106.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 135-137°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M326190

Florfenicol intermediate.

REFERENCES

• Shahit, I., et al.: Drugs, 28, 281 (1984)
• Rogan, M., et al.: Anal. Biochem., 208, 343 (1984)
• Raggi, M., et al.: J. Pharma. Biomed. Anal., 18, 193 (1984)