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We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha1-->2)GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative.

Original publication

DOI

10.1016/j.bmcl.2009.05.095

Type

Journal article

Journal

Bioorg Med Chem Lett

Publication Date

01/08/2009

Volume

19

Pages

4288 - 4291

Keywords

Animals, Antigens, CD1d, Antineoplastic Agents, Cell Line, Tumor, Chemistry, Pharmaceutical, Drug Design, Galactosylceramides, Glycosides, Humans, Killer Cells, Natural, Mice, Models, Chemical, Th2 Cells