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

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.
1523-7060
4433-4436
Leung, Leo
bc749c61-15c6-4c7c-9396-db2c93ac3fd9
Tomassi, Cyrille
51fbf42e-4b91-481c-8528-95ca06e30c40
Van Beneden, Katrien
d8fc2c97-163b-4422-a513-34a08745a00c
Decruy, Tine
0d799625-7310-423a-b7a7-6ece86b8ea1a
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
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
973ff46f-46f1-4d7c-b27d-0f53221e4c44
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Leung, Leo
bc749c61-15c6-4c7c-9396-db2c93ac3fd9
Tomassi, Cyrille
51fbf42e-4b91-481c-8528-95ca06e30c40
Van Beneden, Katrien
d8fc2c97-163b-4422-a513-34a08745a00c
Decruy, Tine
0d799625-7310-423a-b7a7-6ece86b8ea1a
Elewaut, Dirk
98c0d9e0-e559-4f19-8a56-573fee3da83e
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
973ff46f-46f1-4d7c-b27d-0f53221e4c44
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

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).

Record type: Article

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
ORCID for Tim Elliott: ORCID iD orcid.org/0000-0003-1097-0222
ORCID for Joern Werner: ORCID iD orcid.org/0000-0002-4712-1833
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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

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Contributors

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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