| Literature DB >> 18798635 |
Leo Leung1, Cyrille Tomassi, Katrien Van Beneden, Tine Decruy, Dirk Elewaut, Tim Elliott, Aymen Al-Shamkhani, Christian Ottensmeier, Serge Van Calenbergh, Joern Werner, Tony Williams, Bruno Linclau.
Abstract
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.Entities:
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Year: 2008 PMID： 18798635 DOI： 10.1021/ol801663m
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005