(2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-acetamidooctadec-4-en-1-yl benzoate

• ChemBase ID: 163498
• Molecular Formular: C33H57NO4Si
• Molecular Mass: 559.89548
• Monoisotopic Mass: 559.40568584
• SMILES: C(CCCCCCCCCCC/C=C/[C@H]([C@H](COC(=O)c1ccccc1)NC(=O)C)O[Si](C(C)(C)C)(C)C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)C)COC(=O)c1ccccc1)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C33H57NO4Si/c1-8-9-10-11-12-13-14-15-16-17-18-19-23-26-31(38-39(6,7)33(3,4)5)30(34-28(2)35)27-37-32(36)29-24-21-20-22-25-29/h20-26,30-31H,8-19,27H2,1-7H3,(H,34,35)/b26-23+/t30-,31+/m0/s1
• InChIKey: PDVWOLYQMMMSDZ-MQBRABDUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-acetamidooctadec-4-en-1-yl benzoate
• IUPAC Traditional name: (2S,3R,4E)-3-[(tert-butyldimethylsilyl)oxy]-2-acetamidooctadec-4-en-1-yl benzoate
• Synonyms: 2-O-tert-Butyldimethylsilyl-1-O-benzoyl-N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]acetamide; 2-O-tert-Butyldimethylsilyl-1-O-benzoyl-N-acetyl-D-sphingosine; 2-O-tert-Butyldimethylsilyl-1-O-benzoyl Acetyl Ceramide; 2-O-tert-Butyldimethylsilyl-1-O-benzoyl N-Acetylsphingosine; 2-O-tert-Butyldimethylsilyl-1-O-benzoyl C2 Ceramide

Database IDs

• PubChem SID: 162257633
• PubChem CID: 71314457

CALCULATED PROPERTIES

• Acid pKa: 13.506264
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 9.3392
• LogD (pH = 7.4): 9.3392
• Log P: 9.3392
• Molar Refractivity: 161.0059 cm^3
• Polarizability: 65.390656 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Viscous Oil

DETAILS

Toronto Research Chemicals - B699115

C2 Ceramide (C262500) derivative.