Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3259-3262

  Smelt, Kathryn H ^a,d   Harrison, Amanda J ^a   Biggadike, Keith ^b   Müller, Mathias ^c   Prout, Keith ^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; AZIDE; BICYCLO COMPOUND; FUCOSE; PYRANOSIDE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CRYSTAL STRUCTURE; HYDROGENATION; HYDROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033574622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00378-0     Document Type: Article

References (15)

1. Ferrier, RJ; Furneaux, RH Aust. J. Chem., 1980, 33, 1025; Ohrui, H; Horiki, H; Kishi, H; Meguro, H Agric. Biol. Chem., 1983, 47, 1101; Somsak, L; Ferrier, J. Adv. Carbohydr. Chem. Biochem., 1991, 49, 37; Osz, E; Sos, E; Somsak, L; Szilagyi, L; Dinya, Z Tetrahedron, 1997, 53, 5813.
2. Ferrier, RJ; Furneaux, RH Aust. J. Chem., 1980, 33, 1025; Ohrui, H; Horiki, H; Kishi, H; Meguro, H Agric. Biol. Chem., 1983, 47, 1101; Somsak, L; Ferrier, J. Adv. Carbohydr. Chem. Biochem., 1991, 49, 37; Osz, E; Sos, E; Somsak, L; Szilagyi, L; Dinya, Z Tetrahedron, 1997, 53, 5813.
3. Ferrier, RJ; Furneaux, RH Aust. J. Chem., 1980, 33, 1025; Ohrui, H; Horiki, H; Kishi, H; Meguro, H Agric. Biol. Chem., 1983, 47, 1101; Somsak, L; Ferrier, J. Adv. Carbohydr. Chem. Biochem., 1991, 49, 37; Osz, E; Sos, E; Somsak, L; Szilagyi, L; Dinya, Z Tetrahedron, 1997, 53, 5813.
4. Ferrier, RJ; Furneaux, RH Aust. J. Chem., 1980, 33, 1025; Ohrui, H; Horiki, H; Kishi, H; Meguro, H Agric. Biol. Chem., 1983, 47, 1101; Somsak, L; Ferrier, J. Adv. Carbohydr. Chem. Biochem., 1991, 49, 37; Osz, E; Sos, E; Somsak, L; Szilagyi, L; Dinya, Z Tetrahedron, 1997, 53, 5813.
5. Smelt, KH; Blériot, Y; Biggadike, K; Lynn, S; Lane, AL; Watkin, DJ; Fleet, GWJ preceding publication.
6. Beacham, A; Smelt, KH; Biggadike, K; Britten, CJ; Hackett, L; Winchester, BG; Nash, RJ; Griffiths, RC; Fleet, GWJ Tetrahedron Lett., 1998, 39, 151.
7. Jeffries, I; Bowen, BR Bioorg. Med. Chem. Lett., 1997, 7, 1171 and references cited therein.
8. The atomic coordinates for the triazene 5 and the methyl glycoside 15 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.
9. 3,4 4.8 Hz), 5.98 (1H, s, H-7).
10. +, 100%).
11. 3), 69.1, 70.3, 71.0, 73.1, 75.4 (C-3,4,5,6,7), 96.8 (C-2), 170.5 (C=O).
12. Dimroth, O Ber., 1907, 40, 2376.
13. Gaoni, Y J. Org. Chem., 1994, 59, 6853.
14. 6,5 4.9 Hz), 5.12 (1H, s, H-7).
15. This work was supported by a GlaxoWellcome studentship to KHS. All new compounds in this paper have microanalytical and/or spectroscopic data consistent with the structures proposed.