tert-butyl N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate

• ChemBase ID: 162644
• Molecular Formular: C23H45NO4
• Molecular Mass: 399.6077
• Monoisotopic Mass: 399.33485893
• SMILES: OC[C@H](NC(=O)OC(C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)OC(C)(C)C)CO)O
• InChI: InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(26)20(19-25)24-22(27)28-23(2,3)4/h17-18,20-21,25-26H,5-16,19H2,1-4H3,(H,24,27)/b18-17+/t20-,21+/m0/s1
• InChIKey: UMUDVBSIURBUGW-BWMVHVDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
• Synonyms: [(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]carbamic Acid 1,1-Dimethylethyl Ester; [R-[R*,S*-(E)]]-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]carbamic Acid 1,1-Dimethylethyl Ester; (4E,2S,3R)-1,3-Dihydroxy-2-((tert-butoxycarbonyl)amino)-4-octadecene; N-(tert-Butoxycarbonyl)-D-erythro-sphingosine; N-Boc-erythro-sphingosine

Database IDs

• CAS Number: 116467-63-1
• PubChem SID: 162256779
• PubChem CID: 10949378

CALCULATED PROPERTIES

• Acid pKa: 13.768949
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 6.058677
• LogD (pH = 7.4): 6.058677
• Log P: 6.0586777
• Molar Refractivity: 116.765 cm^3
• Polarizability: 45.986855 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 59-60°C

DETAILS

Toronto Research Chemicals - B667750

The N-Boc protected 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.