(2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2,2-dimethylpropanoate

• ChemBase ID: 160984
• Molecular Formular: C29H57N3O3Si
• Molecular Mass: 523.86668
• Monoisotopic Mass: 523.41691923
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C)(C)C(C)(C)C)N=[N+]=[N-])C(=O)C(C)(C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COC(=O)C(C)(C)C)N=[N+]=[N-])O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C29H57N3O3Si/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26(35-36(8,9)29(5,6)7)25(31-32-30)24-34-27(33)28(2,3)4/h22-23,25-26H,10-21,24H2,1-9H3/b23-22+/t25-,26+/m0/s1
• InChIKey: DFUOSUDIKSYZMW-AMGHMTOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2,2-dimethylpropanoate
• IUPAC Traditional name: (2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl 2,2-dimethylpropanoate
• Synonyms: (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyl)-1-pivaloyl-erythro-sphingosine; (2S,3R,4E)-2-Azido-3-(tertbutyldimethylsilyloxy)-1-pivaloyloxy-4-octadecene-3-ol

Database IDs

• CAS Number: 114275-42-2
• PubChem SID: 162255119
• PubChem CID: 14101940

CALCULATED PROPERTIES

• Acid pKa: 16.683914
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 9.8073
• LogD (pH = 7.4): 9.8073
• Log P: 9.8674
• Molar Refractivity: 149.229 cm^3
• Polarizability: 60.544643 Å^3
• Polar Surface Area: 64.96 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - A822575

A derivative of Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isom