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

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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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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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Published date: 16 October 2008


Local EPrints ID: 147925
ISSN: 1523-7060
PURE UUID: 47f170cd-a834-4343-ae6f-32fdfaebb125
ORCID for Tim Elliott: ORCID iD
ORCID for Joern Werner: ORCID iD
ORCID for Bruno Linclau: ORCID iD

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Date deposited: 27 Apr 2010 08:19
Last modified: 18 Jul 2017 19:33

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Author: Leo Leung
Author: Cyrille Tomassi
Author: Katrien Van Beneden
Author: Tine Decruy
Author: Dirk Elewaut
Author: Tim Elliott ORCID iD
Author: Serge Van Calenbergh
Author: Joern Werner ORCID iD
Author: Tony Williams
Author: Bruno Linclau ORCID iD

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