Journal
ORGANIC LETTERS
Volume 10, Issue 20, Pages 4433-4436Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801663m
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- Cancer Research Technology
- Research Flanders (FWO-Vlaanderen)
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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.
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