Ring contraction of glycopyranosyl enamines: An easy route to furanoid thioglycosides of 5-aminosugars

Tetrahedron Asymmetry

Volumn 15, Issue 13, 2004, Pages 2003-2010

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

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMINOGLYCOSIDE DERIVATIVE; CARBOHYDRATE DERIVATIVE; ENAMINE; HYDROXYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOGLYCOSIDE; THIOL DERIVATIVE;

ARTICLE; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; ULTRAVIOLET SPECTROSCOPY;

EID: 3142532633     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.05.027     Document Type: Article

References (30)

1. Pradera M.A., Olano D., Fuentes J. Tetrahedron Lett. 36:1995;8653-8656
2. Fuentes J., Olano D., Pradera M.A. Tetrahedron: Asymmetry. 8:1997;3443-3456
3. Pradera, M. A.; Olano, D.; Sayago, F. J.; Gasch, C.; Illangua, J. M.; Repetto, G.; Fuentes, J. Communicated at 23rd IUPAC International Symposium on the Chemistry of Natural Products, Florence, Italy, 2002. Book of abstracts, communication P73, p 199
4. Fuentes J., Gasch C., Olano D., Pradera M.A., Repetto G., Sayago F.J. Tetrahedron: Asymmetry. 13:2002;1743-1753
5. For a recent review see: Lillelund V.H., Jensen H.H., Liang X., Bols M. Chem. Rev. 102:2002;515-553
6. Fuentes J., Olano D., Gasch C., Pradera M.A. Tetrahedron: Asymmetry. 11:2000;2471-2482
7. Babiano Caballero R., Fuentes Mota J., Galbis Pérez J.A. Carbohydr. Res. 154:1986;208-288
8. For a review see: García Fernández J.M., Ortiz Mellet C. Adv. Carbohydr. Chem. Biochem. 55:1999;35-135
9. For a review see: Garegg P.J. Adv. Carbohydr. Chem. Biochem. 52:1997;179-205
10. Zhang Z., Ollmann I.R., Ye X.-S., Wischnat R., Baarov T., Wong Ch.-H. J. Am. Chem. Soc. 121:1999;734-753
11. See as examples: Crich D., Li H. J. Org. Chem. 67:2002;4640-4646
12. Crich D., Mora M.de la, Vinod A.U. J. Org. Chem. 68:2003;8142
13. Das S.K., Roy J., Reddy K.A., Abbieni C. Carbohydr. Res. 338:2003;2237-2240
14. Van der Klein P.A.M., Boons G.J.P.H., Veeneman G.H., Van der Marel G.A., Van Boom J.H. Synlett. 1990;311-313
15. Brennan P.J., Nikaido H. Annu. Rev. Biochem. 64:1995;29-63
16. Lederkremer R.M., Colli W. Glycobiology. 5:1995;547-552
17. Ayer W.A., Kawahara N. Tetrahedron Lett. 36:1995;7953-7956
18. Kils F.M. New Compr. Biochem. 29a:1995;511
19. Gelin M., Ferrières V., Plusquellec D. Eur. J. Org. Chem. 2000;1423-1431
20. See as examples: Cociorva O.M., Lowary T.L. Tetrahedron. 60:2004;1481-1489
21. Pathak A.K., Pathak V., Kulshrestha M., Kinnaird D., Suling W.J., Gurcha S.S., Besra G.S., Reynolds R.C. Tetrahedron. 59:2003;10239-10248
22. D'Souza F.W., Cheshev P.E., Ayers J.D., Lowary T.L. J. Org. Chem. 63:1998;9037-9044
23. Misra A.K., Agnihotri G. Carbohydr. Res. 339:2004;885-890
24. Bozo E., Boros S., Kuszmann J. Carbohydr. Res. 311:1998;191-202
25. Pradera M.A., Sayago F.J., Illangua J.M., Gasch C., Fuentes J. Tetrahedron Lett. 44:2003;6605-6608
26. Fuentes J., Sayago F.J., Illangua J.M., Gasch C., Angulo M., Pradera M.A. Tetrahedron: Asymmetry. 15:2004;603-615
27. Gómez Sánchez A., Gómez Guillén M., Cert Ventulá A., Scheidegger V. An. Real Soc. Esp. Fis. Quim. 64:1968;579-590
28. Bock K., Pedersen C. Adv. Carbohydr. Chem. Biochem. 41:1983;27-67
29. Bax A., Summers M.F. J. Am. Chem. Soc. 108:1986;2093-2094
30. Stott K., Keeler J., Van Q.N., Shaka A.J. J. Magn. Reson. 125:1997;302-324