Photobromination of a bicyclic mimic of α-L-fucose; components for a combinatorial library of rigid fucose analogues

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3255-3258

  Smelt, Kathryn H ^a,d   Blériot, Yves ^a   Biggadike, Keith ^b   Lynn, Sean ^b   Lane, Alexandra L ^c   Watkin, David J ^c   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d Formerly CombiChem Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA L FUCOSE DERIVATIVE; BICYCLO COMPOUND; FUCOSE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; HYDROLYSIS; ISOMER; REDUCTION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033574651     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00377-9     Document Type: Article

References (28)

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7. Mai, JK; Krajewski, S; Reifenberger, G; Genderski, B; Lensing Hohn, S; Ashwell, KWS Neurosci., 1999, 88, 847; Baisch, G; Ohrlein, R Biorg.Med. Chem., 1998, 6, 1675; Sears, P; Wong, CH Chem. Commun., 1998, 1161; Hitoshi, S; Kusunoki, S; Kanazawa, I; Tsuji, S., J. Neurochem., 1998, 70, 2174; Havenaar, EC; Hoff, RC; vandenEijnden, DH; vanDijk, W Glycoconj. J., 1998, 15, 389; MartinSatue, M; Marrugat, R; Cancelas, JA; Blanco, JJ. Cancer Res., 1998, 58, 1544; Wischnat, R; Martin, R; Wong, CH J. Org. Chem., 1998, 63, 8361; Fleming, CJ; Sinclair, DU; White, EJ; Winchester, B; Whiteford, ML; Connor, JM J. Inherited Metabol. Disease, 1998, 21, 688; Matsuura, N; Narita, T; Hiraiwa, N; Hiraiwa, M; Murai, H; Iwase, Y; Funahashi, H; Imai, T; Takagi, H; Kannagi, R Int. J. Oncology , 1998, 12, 1157.
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18. 6,5 3.4 Hz), 5.16-5.21 (3H, m, H-3,4,5), 6.42 (1H, s, H-7).
19. The atomic coordinates for the bromide 7 are available on request from the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW; the crystallographic numbering system differs from that used elsewhere in the text. Any request should be accompanied by the full literature citation for this paper.
20. 4,3 4.8 Hz).
21. The atomic coordinates for the azide 4 are available on request from the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW; the crystallographic numbering system differs from that used elsewhere in the text. Any request should be accompanied by the full literature citation for this paper.
22. 6,5 4.0 Hz), 5.75 (1H, s, H-7).
23. 7,6 4.2 Hz).
24. 6,5 3.4Hz), 5.98 (1H, s, H-7), 7.44-7.47 (2H, m, 2 × CH(Ar)), 7.54 (1H, t, CH(Ar), J 7.4 Hz), 7.83 (2H, d, 2 × CH(Ar), J 7.3 Hz).
25. 6,5 3.9 Hz), 5.97 (s, 1H, H-7), 8.03, 8.32 (2 × 2H, 2 × d, 4 × CH(Ar), J 8.8 Hz).
26. 6,5 4.2 Hz), 5.35 (s, 1H, H-7), 7.33, 7.76 (2 × 2H, 2 × d, Ar, J 8.2 Hz).
27. Smelt, KH; Harrrison, AJ; Biggadike, K; Muller, M; Prout, CK; Watkin DJ; Fleet, GWJ following paper.
28. This work was supported by a GlaxoWellcome studentship to KHS. All new compounds in this paper have microanalytical and spectroscopic data consistent with the structures proposed except for the amines 8 and 6, which have been characterised on the basis of spectroscopic evidence only.