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The synthesis of 4-deoxy-4,4-difluoro-KRN7000 starting from phytosphingosine is described. Key steps include a regioselective benzylation of azidophytosphingosine and a deoxofluor-mediated fluorination of the corresponding 4-ketone. This fluorination failed completely when the adjacent 3-OH was protected as benzyl ether but proceeded well when a benzoyl group was used. The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation.

Original publication

DOI

10.1021/ol801663m

Type

Journal article

Journal

Organic letters

Publication Date

10/2008

Volume

10

Pages

4433 - 4436

Addresses

School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.

Keywords

Killer Cells, Natural, Animals, Mice, Inbred C57BL, Mice, Benzene, Galactosylceramides, Cytokines, Molecular Structure