Abstract
The following compounds were prepared by chemical synthesis from tribenzoylsphingosine: (2S,3S,4S)-2-acetamido-1,3,4-trihydroxyoctadecane, (2S,3S,4R)-2-acetamido-1,3,4-triydroxyoctadecane, (2S,3S,5S)-2-acetamido-1,3,5-trihydroxyoctadecane, and (2S,3S,5R)-2-acetamido-1,3,5-trihydroxyoctadecane. These compounds were characterized by melting point determination, low and high resolution mass spectra, infrared, optical rotation, chromatographic, and chemical degradation studies. In addition, each of the compounds was converted to the corresponding free base and N-benzoyl derivative. (2S,3S,4R)-2-Benzylamino-1,3,4-trihydroxyoctadecane was prepared from the N-benzoyl derivative of authentic phytosphingosine.
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