Stereocontrolled synthesis of iminocyclitols with an ether bridge

Tetrahedron

Volumn 63, Issue 22, 2007, Pages 4695-4702

  Sayago, Francisco J ^a   Fuentes, José ^a   Angulo, Manuel ^a   Gasch, Consolación ^a   Angeles Pradera M ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Atropoisomerism; Bicyclic azasugars; Iminocyclitols

Indexed keywords

CARBOHYDRATE DERIVATIVE; ETHER DERIVATIVE; IMINOCYCLITOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 34247195455     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.097     Document Type: Article

References (29)

1. See as examples:
2. Afarinkia K., and Bahar A. Tetrahedron: Asymmetry 12 (2005) 1239-1287
3. Lillelund V.H., Jensen H., Liang X., and Bols M. Chem. Rev. 102 (2002) 515-553
4. Stutz A.E. Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond (1999), Wiley-VCH, Weinheim
5. Sinnot M.L. Chem. Rev. 90 (1990) 1171-1202
6. Winchester B., and Fleet G.W.G. Glycobiology 2 (1992) 199-210
7. Winkler D.A., and Holan G. J. Med. Chem. 32 (1989) 2084-2089
8. Giannis A. Angew. Chem., Int. Ed. Engl. 33 (1994) 178-180
9. For a review see:. Casiraghi G., Zanardi F., Rassu G., and Spanu P. Chem. Rev. 95 (1995) 1677-1716
10. See as examples:
11. Blanco M.-J., and Sardina F.J. J. Org. Chem. 63 (1998) 3411-3416
12. Fuentes J., Gasch C., Olano D., Pradera M.A., Repetto G., and Sayago F.J. Tetrahedron: Asymmetry 13 (2002) 1743-1753
13. Chabeaud L., Landais Y., and Renaud P. Org. Lett. 7 (2005) 2587-2590
14. Li H., Blériot Y., Chantereau C., Mallet J.M., Sollogoub M., Zhang Y., Rodriguez-García E., Vogel P., Jimenez-Barbero J., and Sinay P. Org. Biomol. Chem. 2 (2004) 1492-1499
15. Kilonda A., Dequeker E., Compernolle F., Delbeke P., Toppet S., Babady B., and Hoornaert G.J. Tetrahedron 51 (1995) 849-858
16. Poitout L., Le Merrer Y., and Depezay J.C. Tetrahedron Lett. 37 (1996) 1613-1616
17. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 12 (2005) 1239-1287
18. Asano N., Kato A., Miyauchi M., Kizu H., Tamimori T., Matsui K., Nash R.J., and Molyneux R.J. Eur. J. Biochem. 248 (1997) 296
19. Ball C.P., Barret A.G.M., Poitout L.F., Smith M.L., and Thorn Z.E. Chem. Commun. (1998) 2453-2454
20. Fuentes J., Illangua J.M., Sayago F.J., Angulo M., Gasch C., and Pradera M.A. Tetrahedron: Asymmetry 15 (2004) 3783-3789
21. Sano H., Mio S., Kitagawa J., and Sugai S. Tetrahedron: Asymmetry 5 (1994) 2233-2240
22. Wong C.H., Proveucher L., Porco J.A., Jung S.H., Wang Y.F., Chen L., Wang R., and Steensma D.H. J. Org. Chem. 60 (1995) 1492-1501
23. Fuentes J., Salameh B.A.B., Pradera M.A., Fernández de Córdoba F.J., and Gasch C. Tetrahedron 62 (2006) 97-111 and references cited therein
24. Sayago F.J., Pradera M.A., Gasch C., and Fuentes J. Tetrahedron 62 (2006) 915-921
25. Jeener J., Meier B.H., Bachmann P., and Ernst R.R. J. Chem. Phys. 71 (1979) 4546-4553
26. Perrin C.L., and Dwyer T.J. Chem. Rev. 90 (1990) 935-967
27. Shanan-Atidi H., and Br-Eli K.H. J. Phys. Chem. 74 (1970) 961-968
28. Oki M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry (1985), VCH, Weinheim Chapter 1
29. The minimization was performed through the MM2 force field as implemented in the program ChemOffice. Chem3D version Ultra 9.0. CambridgeSoft Corporation: Cambridge, MA. See: Burkert, H.; Allinger, N. L. Molecular Mechanics; ACS Monography 177; American Chemical Society: Washington, DC, 1982.