(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid

• ChemBase ID: 146887
• Molecular Formular: C16H15NO4
• Molecular Mass: 285.2946
• Monoisotopic Mass: 285.10010797
• SMILES: c1ccc(cc1)[C@@H]([C@H](C(=O)O)O)NC(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)N[C@H]([C@H](C(=O)O)O)c1ccccc1
• InChI: InChI=1S/C16H15NO4/c18-14(16(20)21)13(11-7-3-1-4-8-11)17-15(19)12-9-5-2-6-10-12/h1-10,13-14,18H,(H,17,19)(H,20,21)/t13-,14+/m0/s1
• InChIKey: HYJVYOWKYPNSTK-UONOGXRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid
• IUPAC Traditional name: (2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoic acid
• Synonyms: N-Benzoyl-(2R,3S)-3-phenylisoserine; (αR,βS)-β-(Benzoylamino)-α-hydroxybenzenepropanoic Acid; [R-(R*,S*)]-β-(benzoylamino)-α-hydroxybenzenepropanoic Acid; (2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropionic Acid; (2R,3S)-N-Benzoyl-3-phenylisoserine; (2R,3S)-N-Benzoyl-3-phenyl Isoserine; (2R,3S)-3-Benzamido-2-hydroxy-3-phenylpropanoic acid; N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸

Database IDs

• CAS Number: 132201-33-3
• MDL Number: MFCD00274633
• PubChem SID: 24868119; 162241079
• PubChem CID: 2762289

CALCULATED PROPERTIES

• Acid pKa: 3.6921208
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.025214426
• LogD (pH = 7.4): -1.4769937
• Log P: 1.83164
• Molar Refractivity: 76.4381 cm^3
• Polarizability: 29.423927 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 169-172 °C(lit.)
• Optical Rotation: [α]20/D -40°, c = 1.0 in ethanol

Safety Information

• Storage Condition: Refrigerator
• 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: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 98%
• Linear Formula: C6H5CONHCH(C6H5)CH(OH)CO2H

DETAILS

Sigma Aldrich - 444375

Packaging
500 mg in glass bottle
Application
The presence of this chiral side chain has proven to be essential for the biological activity of taxol,1,2,3 one of the most promising anticancer agents being investigated.4,5 The challenging synthesis of taxol has stimulated interest in the attachment of the C-13 side chain to naturally derived taxanes like baccatin III.6,7,8

Toronto Research Chemicals - B208550

(2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral and immunomodulatory

REFERENCES

• Paal, K. et al.: Bioorg. Med. Chem., 15, 1323 (2007)
• Krawczyk, E. et al.: J. Pharm. Pharmacol., 57, 791 (2007)