Synthesis of C8-glycomimetics as potential glycosidases inhibitors

Tetrahedron Letters

Volumn 45, Issue 43, 2004, Pages 8043-8046

  Andriuzzi, Olivia ^a   Gravier Pelletier, Christine ^a   Le Merrer, Yves ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Aminocyclitols; Carbasugars; Cyclic sulfate; Glycomimetics; Reductive amination

Indexed keywords

GLYCOSIDASE INHIBITOR;

AMINATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; HYDROBORATION; OXIDATION; REACTION ANALYSIS; REDUCTION; RING CLOSING METATHESIS;

EID: 4644287577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.172     Document Type: Article

References (33)

1. S.A. Ross, E.A. Gulve, and M. Wang Chem. Rev. 104 2004 1255
2. P. Zimmel, K.G.M.M. Alberti, and J. Shaw Nature 414 2001 782
3. V.V. Sazak, J.M. Ordovas, A.D. Elbein, and R.W. Berninger Biochem. J. 232 1985 759
4. B. Woynaroska, H. Wilkiel, M. Sharma, N. Carpenter, G.W.J. Fleet, and R.J. Bernacki Anticancer Res. 12 1992 161
5. Y. Chapleur Carbohydrate Mimics, Concepts and Methods 1998 Wiley-VCH New York
6. A.E. Stütz Iminosugars as Glycosidase Inhibitors, Nojirimycin and Beyond 1999 Wiley-VCH Weiheim
7. For C8-carbasugars, see, for example, J. Thiem, and B. Werschkun Angew. Chem., Int. Ed. 36 1997 2793
8. I. Hanna, and L. Ricard Org. Lett. 2 2000 2651
9. P.A.V. van Hooft, E.J.N. Litjens, G.A. van der Marel, C.A.A. van Boeckel, and J.H. van Boom Org. Lett. 3 2001 731
10. P.A.V. van Hooft, G.A. van der Marel, C.A.A. van Boeckel, and J.H. van Boom Tetrahedron Lett. 42 2001 1769
11. F.D. Boyer, I. Hanna, and S.P. Nolan J. Org. Chem. 66 2001 4094
12. J. McNulty, V. Grunner, and J. Mao Tetrahedron Lett. 42 2001 5609
13. Y. Blériot, A. Giroult, J.-M. Mallet, E. Rodriguez, P. Vogel, and P. Sinaà Tetrahedron: Asymmetry 13 2002 2553
14. J. Marco-Contelles, and E. de Opazo J. Org. Chem. 67 2002 3705
15. G. Godin, E. Garnier, P. Compain, O.R. Martin, K. Ikeda, and N. Asano Tetrahedron Lett. 45 2004 579
16. A. Mitrakou, N. Tountas, A.E. Raptis, R.J. Bauer, H. Schulz, and S.A. Raptis Diabetic Med. 15 1998 657
17. B. Gaudillère A.M. Doherty Annu. Rep. Med. Chem. Vol. 34 1999 Academic 317 325
18. K. Matsumoto, M. Yano, and S. Miyake Diabetes Care 21 1998 256
19. C. Gravier-Pelletier, W. Maton, G. Bertho, and Y. Le Merrer Tetrahedron 59 2003 8721 and references cited therein
20. C. Gravier-Pelletier, O. Andriuzzi, and Y. Le Merrer Tetrahedron Lett. 43 2002 245
21. J.M. Brown, K.-W. Kim, T.E. Cole, and B. Singaram J. Am. Chem. Soc. 108 1986 6761
22. A modification of the diastereoselectivity was tentatively carried out in the presence of bulky borane such as 9-BBN or catechol borane, but revealed unsuccessful
23. All new compounds were characterised by analytical and spectroscopic data. Yields are given for isolated, chromatographically purified compounds
24. E. Fernandez, K. Maeda, M.W. Hooper, and J.M. Brown Chem. Eur. J. 6 2000 1840
25. R.J. Mattson, K.M. Pham, D.J. Leuck, and K.A. Cowen J. Org. Chem. 55 1990 2552
26. 2
27. 1H NMR studies (500 MHz) using 2D-COSY and 2D-TOCSY experiments
28. S. Barett, P. O'Brien, H.C. Steffens, T.D. Towers, and M. Voith Tetrahedron 56 2000 9633
29. 2-axis of symmetry displayed by the d-manno- or l-ido-cyclooctene 1 or 2, only a single stereoisomer can be obtained during the syn-epoxidation or the syn-dihydroxylation towards the respective 15, 16 and 17, 18 derivatives
30. Y. Gao, and K.B. Sharpless J. Am. Chem. Soc. 110 1988 7538
31. J.M. Dougherty, D.A. Probst, R.E. Robinson, J.D. Moore, T.A. Klein, K.A. Snelgrove, and P.R. Hanson Tetrahedron 56 2000 9781
32. B. Moon Kim, and K.B. Sharpless Tetrahedron Lett. 30 1989 655
33. C. Gravier-Pelletier, W. Maton, T. Dintinger, C. Tellier, and Y. Le Merrer Tetrahedron 59 2003 8705