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An efficient synthesis ofd-ribo-C18-phytosphingosine andl-arabino-C18-phytosphingosine fromd-fructose

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
67
Issue
48
Identifiers
DOI: 10.1016/j.tet.2011.10.003
Keywords
  • Phytosphingosines
  • Sphingolipids
  • Olefin Cross-Metathesis
  • D-Fructose

Abstract

Abstract d- ribo-C 18-phytosphingosine and l- arabino-C 18-phytosphingosine were synthesised starting from commercially inexpensive d-fructose. Metal-mediated fragmentation and stereoselective reduction were used as key steps to provide the hydrophilic portion of d- ribo and l- arabino phytosphingosines. Grubbs’ cross-metathesis and hydrogenation allowed the incorporation of hydrophobic tail.

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