Collect. Czech. Chem. Commun.
2005, 70, 2075-2085
https://doi.org/10.1135/cccc20052075
Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion
Jiří Kroutil* and Klára Jeništová
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, 128 43 Prague 2, Czech Republic
References
1. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91.
< T.: https://doi.org/10.1016/S0065-2318(08)60032-3>
2. Curr. Org. Chem. 1999, 3, 287.
K., Albert M., Ortner J., Paul B. J.:
3. J. Med. Chem. 2005, 48, 3736.
< J. N., Jin Y. H., Rapp K. L., Bennett M., Schinazi R. F. Chu C. K.: https://doi.org/10.1021/jm050096d>
4. Antimicrob. Agents Chemother. 2005, 49, 560.
< G., Hurwitz S. J., Gumina G., Chu C. K., McClure H. M., Schinazi R. F.: https://doi.org/10.1128/AAC.49.2.560-564.2005>
5. Bioorg. Med. Chem. Lett. 2005, 15, 1307.
< C. H., Yao S. L., Chiu Y. H., Leung P. Y., Robert N., Seddon J., Sears P., Hwang C. K., Ichikawa Y., Romero A.: https://doi.org/10.1016/j.bmcl.2005.01.027>
6. Chem.-Eur. J. 2005, 11, 3194.
< D. B., Seeberger P. H.: https://doi.org/10.1002/chem.200500025>
7. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 1145.
< C., Foss C. A., Cheong I., Wang Y. C., Diaz L., Agrawal N., Fox J., Dick J., Dang L. H., Zhou S. B., Kinzler K. W., Vogelstein B., Pomper M. G.: https://doi.org/10.1073/pnas.0408861102>
8. Mol. Imag. Biol. 2002, 4, 352.
< J., Černý M.: https://doi.org/10.1016/S1536-1632(02)00083-5>
9. Dax K., Albert M. in: Glyoscience: Epimerisation, Isomerisation and Rearrangement Reactions of Carbohydrates (S. V. Ley, J. Thiem, F. Vogtle, B. M. Trost, H. Yamamoto, A. De Meijere, K. N. Houk, H. Kessler, A. E. Stutz, S. L. Schreiber and J. M. Lehn, Eds), Vol. 215, p. 193. Springer Verlag, Berlin 2001.
10. Carbohydr. Res. 2000, 327, 47.
< K., Albert M., Ortner J., Paul B. J.: https://doi.org/10.1016/S0008-6215(00)00022-7>
11. Tetrahedron Lett. 1992, 33, 7087.
< A. A., Arshava B. M., Mikerin I. E., Raifeld Y. E., Lee V. J., Lang S. A.: https://doi.org/10.1016/S0040-4039(00)60842-0>
12. Černý M. in: Frontiers in Biomedicine and Biotechnology, Levoglucosenone and Levoglucosans, Chemistry and Applications (Z. J. Witczak, Ed.), p. 121. ATL Press, New York 1994.
13. Adv. Carbohydr. Chem. Biochem. 1977, 34, 23.
< M., Staněk J.: https://doi.org/10.1016/S0065-2318(08)60324-8>
14. J. Antibiot. 1985, 38, 1287.
< T., Takahashi Y., Kobayashi Y., Umezawa S., Umezawa H.: https://doi.org/10.7164/antibiotics.38.1287>
15. Carbohydr. Res. 1984, 126, 45.
< T., Ajito K., Umezawa S., Ikeda A.: https://doi.org/10.1016/0008-6215(84)85125-3>
16. Helv. Chim. Acta 1999, 82, 2052.
< I. A., Sivets G. G.: https://doi.org/10.1002/(SICI)1522-2675(19991110)82:11<2052::AID-HLCA2052>3.0.CO;2-7>
17. Eur. J. Org. Chem. 2002, 2002, 2449.
< J., Trnka T., Budešínský M., Černý M.: https://doi.org/10.1002/1099-0690(200208)2002:15<2449::AID-EJOC2449>3.0.CO;2-4>
18. Collect. Czech. Chem. Commun. 2002, 67, 1805.
< J., Karban J., Trnka T., Budešínský M., Černý M.: https://doi.org/10.1135/cccc20021805>
19. Kroutil J.: Ph.D. Thesis. Charles University, Prague 2000.
20. Carbohydr. Res. 2003, 338, 2825.
< J., Karban J., Buděšínský M.: https://doi.org/10.1016/j.carres.2003.07.003>
21. Tetrahedron 2001, 57, 6955.
< H., Joly G. J., Peeters K., Hoornaert G. J., Compernolle F.: https://doi.org/10.1016/S0040-4020(01)00650-0>
22. Synlett 2000, 868.
A., Segat-Dioury F., Nait-Bouda L., Cosma C., Siaugue J. M., Foos J., Guy A.:
23. Greene T. W., Wuts P. G. M.: Protective Groups in Organic Synthesis, 3rd ed. J. Wiley, New York 1999.
24. Chem. Pharm. Bull. 2001, 49, 312.
< M., Ohno A., Yamada S.: https://doi.org/10.1248/cpb.49.312>
25. J. Org. Chem. 2002, 67, 3065.
< S. F., Bergolla L. A., Garcia P. I.: https://doi.org/10.1021/jo0111560>
26. Carbohydr. Res. 1988, 174, 349.
< M., Trnka T., Redlich H.: https://doi.org/10.1016/0008-6215(88)85104-8>
27. Carbohydr. Res. 2005, 340, 503.
< J., Karban J.: https://doi.org/10.1016/j.carres.2004.12.007>
28. Tetrahedron Lett. 1987, 28, 4733.
< P., Camps F., Chamorro E., Gasol V., Guerrero A.: https://doi.org/10.1016/S0040-4039(00)96612-7>
29. J. Fluorine Chem. 2005, 126, 209.
< M., Bujok R.: https://doi.org/10.1016/j.jfluchem.2004.12.003>
30. Tetrahedron Lett. 1991, 32, 7381.
< M.: https://doi.org/10.1016/0040-4039(91)80112-J>
31. Tetrahedron Lett. 2004, 45, 1385.
< M., Bujok R.: https://doi.org/10.1016/j.tetlet.2003.12.078>
32. Fürst A., Plattner P. A.: 12th International Congress of Pure and Applied Chemistry. Abstract of Papers, p. 409, New York 1951.
33. Collect. Czech. Chem. Commun. 1979, 44, 1949.
< M., Trnka T., Černý M.: https://doi.org/10.1135/cccc19791949>