4.7 Article

Synthesis of α-galactosyl ceramide, a potent immunostimulatory agent

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 13, Pages 4559-4564

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo0201530

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alpha-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of alpha-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.

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