Nitrone in L-lyxose series: Cycloaddition way for the synthesis of new C-α-fucosides

Tetrahedron Letters

Volumn 45, Issue 28, 2004, Pages 5363-5366

  Chevrier, Carine ^a   LeNouen, Didier ^a   Neuburger, Markus ^b   Defoin, Albert ^a   Tarnus, Céline ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

1,3 Dipolar addition; Amino sugar; Fucosidase inhibitors; Nitrone; Phosphonate

Indexed keywords

ACETOHYDROXAMIC ACID; ALKENE; AMINOSUGAR; CARBOHYDRATE DERIVATIVE; ETHANE; FUCOSE; LEVO LYXOSE; NITRONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RIBOSE; SULFATE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CYCLOADDITION; REDUCTION; SYNTHESIS;

EID: 2942669882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.075     Document Type: Article

References (23)

1. Fleet G.W.J., Shaw A.N., Evans S.V., Fellows L.E. J. Chem. Soc., Chem. Commun. 1985;841-842
2. Winchester Br., Barker C., Baines S., Jacob G.S., Namgoong S.K., Fleet G.W.J. Biochem. J. 265:1990;277-282
3. Wischnat R., Martin R., Takayama S., Wong C.-H. Bioorg. Med. Chem. Lett. 8:1998;3353-3358
4. Takayama S., Martin R., Wu J., Laslo K., Siusdak G., Wong C.-H. J. Am. Chem. Soc. 119:1997;8146-8151
5. Joubert, M. Ph.D. Thesis, Université de Haute-Alsace (France), 2000
6. Joubert M., Defoin A., Tarnus C., Streith J. Synlett. 9:2000;1366-1368
7. Vasella A. Helv. Chim. Acta. 60:1977;1273-1295
8. Another synthesis of protected 5-deoxyribose 6b was recently published: Jensen H.H., Jensen A., Hazell R.G., Bols M. J. Chem. Soc., Perkin Trans. 1. 2002;1190-1198
9. Holzapfel C.W., Crous R. Heterocycles. 48:1998;1337-1341
10. Mizuno K., Kimura Y., Otsuji Y. Synthesis. 1979;688. Used solvent was ethyl ether in place of benzene (yield 65%)
11. Bayón P., de March P., Figueredo M., Font J. Tetrahedron. 54:1998;15691-15700
12. Chevrier C., Defoin A. Synthesis. 2003;1221-1224
13. DeShong Ph., Dicken C.M., Staib R.R., Freyer A.J., Weinreb St.M. J. Org. Chem. 47:1982;4397-4403
14. Ali Sk.A., Khan J.H., Wazeer M.I.M. Tetrahedron. 44:1988;5911-5920
15. Meske M. J. Prakt. Chem. 339:1997;426-433
16. 21, 22
17. Valerio R.M., Alewood R.F., Johns R.B. Synthesis. 1988;786-789
18. Oshikawa T., Yamashita M. Bull. Chem. Soc. Jpn. 63:1990;2728-2730
19. Seo K. Carbohydr. Res. 119:1983;101-107
20. Vasella A., Meuwly R. Helv. Chim. Acta. 69:1986;751-760
21. Altomare A., Cascarano G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori G., Camalli M. J. Appl. Cryst. 27:1994;435
22. Watkin D.J., Prout C.K., Carruthers J.R., Betteridge P.W., Cooper R.I. Crystals. 2001;Chemical Crystallography Laboratory, Oxford, UK. Issue 11
23. Watkin D.J., Prout C.K., Pearce L.J. Cameron. 1996;Chemical Crystallography Laboratory, Oxford, UK