A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids

Russian Chemical Bulletin

Volumn 49, Issue 7, 2000, Pages 1305-1309

  Kononov, L O ^a   Cheshev, P E ^a   Nifant'ev, N E ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Aglycon; Allyl glycoside; Aminoethyl glycosides; Glycolipids; Oximation; Ozonolysis; Pre spacer; Reduction

Indexed keywords

EID: 0034336776     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02495780     Document Type: Article

References (27)

1. Carbohydrates in Drug Design. Eds. Z. J. Witczak and K. A. Nieforth, 1997, Marcel Dekker Inc., New York, 703 pp.
2. G. Magnusson, A. Ya. Chernyak, J. Kihlberg, and L. O. Kononov, in: Neoglycoconjugates: Preparation and Application, Eds. Y. C. Lee and R. T. Lee, Academic Press Inc., San Diego, California, 1994, 53.
3. L. O. Kononov, A. A. Sherman, A. S. Shashkov, A. V. Kornilov, E. V. Zyryanov, G. V. Zatonsky, and N. E. Nifant'ev, Abstracts of XVIII Internal. Carbohydr. Symp., 1996, July 21-26. Milano, Italy, p. 417, Abstract BPI62.
4. N. E. Nifant'ev. Zh. Ros. Khim. o-va im. D. I. Mendeleeva, 1998. 24, Nos. 1-2, 134 [Russ. Chem. J., 24 (Engl. Transl.)].
5. N. E. Nifant'ev. Zh. Ros. Khim. o-va im. D. I. Mendeleeva, 1998. 24, Nos. 1-2, 134 [Russ. Chem. J., 24 (Engl. Transl.)].
6. R. T. Lee and Y. C. Lee, Carbohydr. Res., 1974, 37, 193.
7. M. A. Bernstein and L. D. Hall, Carbohydr. Res., 1980, 78, Cl.
8. C. R. Bertozzi and M. D. Bednarsky, Carbohydr. Res., 1992, 223, 243.
9. (a). J. Lehmann and L. Ziser, Carbohydr. Res., 1992, 225, 83;
10. (b). J. Lehmann and M. Schmidt-Schuchardt, Carbohydr. Res., 1995, 276, 43.
11. T. - Uchiyama, V. P. Vasilev, T. Kajimoto, W. Wong, H. Huang, C.-C. Lin, and C.-H. Wong, J. Am. Chem. Soc., 1995, 117, 5395.
12. S. J. Danishefsky and M. T. Bilodeau, Angew. Chem., Int. Ed. Engl., 1996, 35, 1380, and references therein.
13. (a). J. Brüning and L. L. Kiesling, Tetrahedron Lett., 1996, 37, 2907;
14. (b). N. Pohl and L. L. Kiesling, Synthesis, 1999, 1515.
15. A. A. Sherman, L. O. Kononov, A. S. Shashkov, G. V. Zatonsky, and N. E. Nifant'ev, Mendeleev Commun., 1998, 9.
16. M. Dubber and T. K. Lindhorst, Carbohydr. Res., 1998, 310, 35.
17. S. Hanessian, A. Benalil, and C. Laferrière, J. Org. Chem., 1995, 60, 4786.
18. M. Hudlicky, Reductions in Organic Chemistry, Ellis Horwood Ltd., Chichester, 1984, p. 309.
19. R. H. Youssef, B. A. Silwanis, R. I. El-Sokkary, A. S. Nematalla, and M. A. Nashed. Carbohydr. Res., 1993, 240, 287.
20. A. H. Haines, Methods for the Oxidation of Organic Compounds. Academic Press, Orlando, 1985, 119.
21. J. March, Advanced Organic Chemistry, J. Wiley and Sons Inc., New York, 1985.
22. P. Angibeaud, J Defaye, A. Gadelle, and J.-P. Utille, Synthesis, 1985, 1123.
23. E. Pretsch, W. Simon, J. Seibl, and T. Clers, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer Verlag, Berlin. 1989, H175, C203.
24. A. Ya. Chernyak, G. V. M. Sharma, L. O. Kononov, P. Radha Krishna, A. B. Levinsky, N. K. Kochetkov, and A. V Rama Rao, Carbohydr. Res., 1992, 223, 303.
25. A. J. Gordon and R. A. Ford, The Chemist Companion. J. Wiley and Sons Inc., New York, 1972.
26. L. O. Kononov, A. V. Kornilov, A. A. Sherman, E. V. Zyryanov, G. V. Zatonskii, A. S. Shashkov, and N. E. Nifant'ev, Bioorgan. Khim., 1998, 24, 608 [Russ. J. Biorg. Chem., 1998, 24 (Engl. Transl.)].
27. L. O. Kononov, A. V. Kornilov, A. A. Sherman, E. V. Zyryanov, G. V. Zatonskii, A. S. Shashkov, and N. E. Nifant'ev, Bioorgan. Khim., 1998, 24, 608 [Russ. J. Biorg. Chem., 1998, 24 (Engl. Transl.)].