Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000

Leung, Leo, Tomassi, Cyrille, Van Beneden, Katrien, Decruy, Tine, Elewaut, Dirk, Elliott, Tim, Al-Shamkhani, Aymen, Ottensmeier, Christian, Van Calenbergh, Serge, Werner, Joern, Williams, Tony and Linclau, Bruno (2008) Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000 Organic Letters, 10, (20), pp. 4433-4436. (doi:10.1021/ol801663m).


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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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1021/ol801663m
ISSNs: 1523-7060 (print)
Related URLs:
Subjects: Q Science > QD Chemistry
R Medicine > R Medicine (General)
R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)
ePrint ID: 147925
Date :
Date Event
16 October 2008Published
Date Deposited: 27 Apr 2010 08:19
Last Modified: 18 Apr 2017 14:35
Further Information:Google Scholar

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