Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000
Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000
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.
4433-4436
Leung, Leo
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Tomassi, Cyrille
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Van Beneden, Katrien
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Decruy, Tine
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Elewaut, Dirk
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Elliott, Tim
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Al-Shamkhani, Aymen
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Ottensmeier, Christian
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Van Calenbergh, Serge
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Werner, Joern
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Williams, Tony
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Linclau, Bruno
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16 October 2008
Leung, Leo
bc749c61-15c6-4c7c-9396-db2c93ac3fd9
Tomassi, Cyrille
51fbf42e-4b91-481c-8528-95ca06e30c40
Van Beneden, Katrien
d8fc2c97-163b-4422-a513-34a08745a00c
Decruy, Tine
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Elewaut, Dirk
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Elliott, Tim
16670fa8-c2f9-477a-91df-7c9e5b453e0e
Al-Shamkhani, Aymen
0a40b3ce-9d71-4d41-9369-7212f0a84504
Ottensmeier, Christian
42b8a398-baac-4843-a3d6-056225675797
Van Calenbergh, Serge
9587a6e2-b48b-4f79-807d-b889c7a1d9d6
Werner, Joern
1b02513a-8310-4f4f-adac-dc2a466bd115
Williams, Tony
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Linclau, Bruno
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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), .
(doi:10.1021/ol801663m).
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.
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Published date: 16 October 2008
Identifiers
Local EPrints ID: 147925
URI: http://eprints.soton.ac.uk/id/eprint/147925
ISSN: 1523-7060
PURE UUID: 47f170cd-a834-4343-ae6f-32fdfaebb125
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Date deposited: 27 Apr 2010 08:19
Last modified: 14 Mar 2024 02:48
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Contributors
Author:
Leo Leung
Author:
Cyrille Tomassi
Author:
Katrien Van Beneden
Author:
Tine Decruy
Author:
Dirk Elewaut
Author:
Serge Van Calenbergh
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