The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

Canadian Journal of Chemistry

Volumn 80, Issue 8, 2002, Pages 857-865

  Best, Wayne M ^a   Macdonald, James M ^a   Skelton, Brian W ^a   Stick, Robert V ^a   Matthew, D ^a   Tilbrook, G ^a   White, Allan H ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

Dihydrooxazine; Glycosidase inhibitors; Iminosugars; Isofagomine; Tetrahydrooxazine

Indexed keywords

AMINES; AROMATIC COMPOUNDS; CATALYSIS; CONFORMATIONS; CRYSTAL STRUCTURE; ENZYMES; HYDROGENATION; HYDROLYSIS; REDUCTION; SINGLE CRYSTALS;

HYDROGENOLYSIS;

CARBOHYDRATES;

ACID; ARABINOSE; ARABINOSIDE; CARBOHYDRATE; CHEMICAL COMPOUND; DIHYDROOXAZINE; GLYCOSIDASE INHIBITOR; ISOFAGOMINE; OXAZINE DERIVATIVE; PALLADIUM; PHTHALIMIDE DERIVATIVE; PYRANOSIDE; TETRAHYDROOXAZINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ENZYME INHIBITION; HEATING; HYDROLYSIS; MITSUNOBU REACTION; REDUCTION; SOLID; STRUCTURE ANALYSIS;

EID: 0036433582     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-060     Document Type: Article

References (25)

1. M.L. Sinnott. Chem. Rev. 90, 1171 (1990).
2. D.L. Zechel and S.G. Withers. Acc. Chem. Res. 33, 11 (2000).
3. G. Legler. Adv. Carbohydr. Chem. Biochem. 48, 319 (1990).
4. B. Ganem. Acc. Chem. Res. 29, 340 (1996).
5. A. E. Stütz (Editor). In Nojirimycin and Beyond. Wiley-VCH, Weinheim. 1999.
6. M. Bols. Acc. Chem. Res. 31, 1 (1998).
7. P. Bach and M. Bols. Tetrahedron Lett. 40, 3461 (1999).
8. S. Hanessian and J.-M. Vatèle. Tetrahedron Lett. 22, 3579 (1981).
9. E.D. Soli, A.S. Manoso, M.C. Patterson, P. DeShong, D.A. Favor, R. Hirschmann, and A.B. Smith, III. J. Org. Chem. 64, 3171 (1999).
10. G. Zhao, U.C. Deo, and B. Ganem. Org. Lett. 3, 201 (2001).
11. G. Pandey and M. Kapur. Tetrahedron Lett. 41, 8821 (2000).
12. T.M. Jespersen, M. Bols, M.R. Sierks, and T. Skrydstrup. Tetrahedron, 50, 13449 (1994).
13. S.U. Hansen and M. Bols. J. Chem. Soc. Perkin Trans. 1, 911 (2000).
14. Y. Ichikawa, Y. Igarashi, M. Ichikawa, and Y. Suhara. J. Am. Chem. Soc. 120, 3007, 5854 (1998).
15. Y.J. Kim, M. Ichikawa, and Y. Ichikawa. J. Org. Chem. 65, 2599 (2000).
16. J. Andersch and M. Bols. Chem. Eur. J. 7, 3744 (2001).
17. M. Bols, R.G. Hazell, and I.B. Thomsen. Chem. Eur. J. 3, 940 (1997).
18. J.C. McAuliffe and R.V. Stick. Aust. J. Chem. 50, 193 (1997).
19. S.R. Hall, D.J. du Boulay, and R. Olthof-Hazekamp (Editors). The Xtal 3.6 System. University of Western Australia, Australia. 2000.
20. J.J. Naleway, C.R.H. Raetz, and L. Anderson. Carbohydr. Res. 179, 199 (1988).
21. R.F. Helm, J. Ralph, and L. Anderson. J. Org. Chem. 56, 7015 (1991).
22. L.R. Schroeder, K.M. Counts, and F.C. Haigh. Carbohydr. Res. 37, 368 (1974).
23. C.K. de Bruyne and G. van der Groen. Carbohydr. Res. 2, 173 (1966).
24. S. Rio, J.-M. Beau, and J.-C. Jacquinet. Carbohydr. Res. 219, 71 (1991).
25. M. Mori, Y. Ito, and T. Ogawa. Carbohydr. Res. 195, 199 (1990).