Powiadomienia systemowe
- Sesja wygasła!
- Sesja wygasła!
- Sesja wygasła!
- Sesja wygasła!
- Sesja wygasła!
Tytuł artykułu
Autorzy
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
Methyl 3,4,5-tri-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enonate (5) was obtained by different routes starting from D-galactose and D-galacturonic acid, respectively. Exploring several protecting group manipulations, an effective route was found out for the preparation of methyl 2,6-anhydro-5-O-benzyl-7,8,9-trideoxy- D-glycero-L-galacto-non-8-enonate (15) which is one of the key compounds in this synthetic program. Finally, selective benzylation via 3,4-O-butylstannyl intermediates resulted in methyl (16) and benzyl (17) 2,6-anhydro-4,5-di-O-benzyl-7,8,9-trideoxy-Dglycero- L-galacto-non-8-enonate both suitable as acceptors in glycosylation reactions. The chemical structure of a great number of intermediates was investigated by X-ray diffraction studies.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
251--265
Opis fizyczny
Bibliogr. 21 poz., rys.
Twórcy
autor
- University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany
autor
- University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany
autor
- University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany
autor
- University of Rostock, Institute of Chemistry, Department of Organic Chemistry, Albert-Einstein-Straße 3a, D-18059 Rostock, Germany
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL-01-224 Warsaw 42, Poland
Bibliografia
- 1.Yamada H., Pectin and Peetinase, Progress in Biotechnology, Eds. J. Visser and A.G.J. Vorage Elsevier, Amsterdam, Vol. 4, 1996, p. 173.
- 2. Kramer S., Nolting B., Ott A.-1., and Vogel C., J. Carbohydn Chem, 19, 891 (2000).
- 3. Vogel C., Nolting B., Kramer S., Stefian W. and Ott A.-J., Advances in Pectin and Pectinase Researc Eds. F. Voragen, H. Schols, R. Visser, Dordrecht-Boston-London, 2003, p. 209.
- 4. Farouk A. and Vogel C., Abstract P3 80, 22nd Intemational Carbohydrate Symposium, Glasgow, United Kingdom, 23-27 July, 2004. Part XIV of the series “Galacturonic Acid Derivatives”, for part XIII see ref. 3.
- 5. Wolfiom M.L. and Thompson A., Methods in Carbohydrate Chemistry, Vol. 2, Eds. R.L. Whistler and M.L. Wolfrom, New York-London, 1963, p. 211.
- 6. Giannis A. and Sandhoff K., Tetrahedron Le!t., 26, 1479 (1985).
- 7. Horton D. and Miyake T., Carbahydr: Res., 184, 221 (1988).
- 8. Pontén F. and Magnusson G., .J. Org. Chem., 61, 7463 (1996).
- 9. Jeflfrey G.A. and Yates J .H., Carbohydn Res., 74, 319 (1979).
- 10. Vogel C., Jeschke U., Vill V. and Fischer H., LiebigsAnn. Chem. , 1 171 (1992), and references therein.
- 11. Jarosz S., Krajewski J.W., Zamojski A.,Duddeck H. and KaiserM., Bull. Pal. Ac: Chem.,33, 181 (1985).
- 12. Krajewsld J.W., Gluziński P., Urbanczyk-Lipkowska Z. and Zamojski A., Carbohydr: Res., 148, 1 (1986). '
- 13. Schmidt and Neukom H., Helv. Chim. Acta, 47, 865 (1964).
- 14.Vogel C., Boye H. and Kristen H., J. Prakt. Chem., 332, 28 (1990).
- 15. Vogel C., Steffan W., Boye H., Kristen H., Betaneli V.I., Ott A.-Ya. and Kochetkov N.K., Carbohydr: Res., 237, 131 (1992). "
- 16. Giese B., Angew. Chem., 101, 993 (1989).
- 17. Kovac P., Carbohydr: Res., 22, 464 (1972).
- 18. David S. and Hanessian S., Tetrahedron, 41, 643 (1985).
- 19. Penin D.D. and Armarego W.L.F., Purification of Laboratory Chemicals. 3rd Ed., Pergamon Press, Oxford, 1988.
- 20. Cabaret D. and Wakselrnan M., .J. Carbohydr: Chem., 10, 55 (1991).
- 21.Hirst E.L. and Percival E., Methods in Carbohydrate Chemistry, Vol. 2, Eds. R.L. Whistler and M.L. Wolfrom, New York-London, 1963, p. 145.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0025-0112