A short and practical route to 3-O-benzoyl azidosphingosine.
A short and practical route to 3-O-benzoyl azidosphingosine from D-xylose is described. The synthesis avoids the use of expensive and hazardous chemicals (i.e. mercury salts), and it is reproducible up to at least a 20 g scale. Furthermore, the synthesis proceeds to 3-O-benzoyl azidosphingosine with a minimum of protection group manipulation, by exploiting a regioselective protection of the primary HO-1 with thexyldimethylsilyl chloride.
Ohlsson
J
J
Organic Chemistry 2, Center for Chemistry, and Chemical Engineering, Lund University, Sweden. jorgen.ohlsson@orgk2.lth.se
Magnusson
G
G
D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C431225:3-O-benzoyl azidosphingosine; D001386:Azides; D007202:Indicators and Reagents; D013110:Sphingosine