N-[(1R,2R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroacetamide

• ChemBase ID: 164059
• Molecular Formular: C17H26Cl2N2O5Si
• Molecular Mass: 437.39024
• Monoisotopic Mass: 436.09880383
• SMILES: c1c(ccc(c1)[C@H]([C@@H](CO[Si](C(C)(C)C)(C)C)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Canonical SMILES: O[C@H](c1ccc(cc1)[N+](=O)[O-])[C@H](NC(=O)C(Cl)Cl)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C17H26Cl2N2O5Si/c1-17(2,3)27(4,5)26-10-13(20-16(23)15(18)19)14(22)11-6-8-12(9-7-11)21(24)25/h6-9,13-15,22H,10H2,1-5H3,(H,20,23)/t13-,14-/m1/s1
• InChIKey: HAFNKEOYFQRWIB-ZIAGYGMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1R,2R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroacetamide
• IUPAC Traditional name: N-[(1R,2R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-1-(4-nitrophenyl)propan-2-yl]-2,2-dichloroacetamide
• Synonyms: 2,2-Dichloro-N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-acetamide; Chloramphenicol O-tert-Butyldimethylsilyl Ether

Database IDs

• CAS Number: 864529-25-9
• PubChem SID: 162258194
• PubChem CID: 71314674

CALCULATED PROPERTIES

• Acid pKa: 8.028616
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.4332087
• LogD (pH = 7.4): 3.3499725
• Log P: 3.4344
• Molar Refractivity: 103.0488 cm^3
• Polarizability: 41.722946 Å^3
• Polar Surface Area: 104.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C325110

Used in the preparation of Azithromycin (A927000) compounds as antibacterial, anti-proliferative, and antiinflammatory agents.