ethyl (2R,3S)-3-[4-(benzyloxy)phenyl]-3-acetamido-2-hydroxypropanoate

• ChemBase ID: 158957
• Molecular Formular: C20H23NO5
• Molecular Mass: 357.40032
• Monoisotopic Mass: 357.15762284
• SMILES: c1c(ccc(c1)[C@@H]([C@H](C(=O)OCC)O)NC(=O)C)OCc1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H]([C@H](c1ccc(cc1)OCc1ccccc1)NC(=O)C)O
• InChI: InChI=1S/C20H23NO5/c1-3-25-20(24)19(23)18(21-14(2)22)16-9-11-17(12-10-16)26-13-15-7-5-4-6-8-15/h4-12,18-19,23H,3,13H2,1-2H3,(H,21,22)/t18-,19+/m0/s1
• InChIKey: HRXCVPWHTCVYKB-RBUKOAKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,3S)-3-[4-(benzyloxy)phenyl]-3-acetamido-2-hydroxypropanoate
• IUPAC Traditional name: ethyl (2R,3S)-3-[4-(benzyloxy)phenyl]-3-acetamido-2-hydroxypropanoate
• Synonyms: (αR,βS)-β-(Acetylamino)-α-hydroxy-4-(phenylmethoxy)-benzenepropanoic Acid Ethyl Ester

Database IDs

• CAS Number: 382596-25-0
• PubChem SID: 162253092
• PubChem CID: 11046536

CALCULATED PROPERTIES

• Acid pKa: 11.964764
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.0469692
• LogD (pH = 7.4): 2.0469577
• Log P: 2.0469694
• Molar Refractivity: 96.3611 cm^3
• Polarizability: 37.92518 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-white Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A161380

Used in the synthesis of Paclitaxel metabolite.