Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2008 Oct 16;10(20):4433-6.
doi: 10.1021/ol801663m. Epub 2008 Sep 18.

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

Leo Leung  1 , 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
Affiliations

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

Leo Leung et al. Org Lett. .

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.

PubMed Disclaimer

Publication types

LinkOut - more resources