tert-butyl N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]carbamate

• ChemBase ID: 162646
• Molecular Formular: C23H47NO4
• Molecular Mass: 401.62358
• Monoisotopic Mass: 401.35050899
• SMILES: OC[C@H](NC(=O)OC(C)(C)C)[C@@H](CCCCCCCCCCCCCCC)O
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@@H](NC(=O)OC(C)(C)C)CO)O
• InChI: InChI=1S/C23H47NO4/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/h20-21,25-26H,5-19H2,1-4H3,(H,24,27)/t20-,21+/m0/s1
• InChIKey: MCEGFLZHNLEUFR-LEWJYISDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]carbamate
• Synonyms: N-[(1S,2R)-2-Hydroxy-1-(hydroxymethyl)heptadecyl]carbamic Acid 1,1-Dimethylethyl Ester; N-tert-Butyloxycarbonyl-D-erythro-dihydro-D-sphingosine

Database IDs

• CAS Number: 140408-14-6
• PubChem SID: 162256781
• PubChem CID: 11773995

CALCULATED PROPERTIES

• Acid pKa: 13.944142
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 6.264692
• LogD (pH = 7.4): 6.2646914
• Log P: 6.264692
• Molar Refractivity: 115.8024 cm^3
• Polarizability: 46.228115 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B667755

Protected D-erythro-C18-Dihydro-D-sphingosine (D449400). Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.

REFERENCES

• Merrill, A.H. Jr., et al.: Biochemistry, 28, 3138 (1989)