Stereoselective synthesis of α- and β-glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates

Journal of the American Chemical Society

Volumn 125, Issue 15, 2003, Pages 4408-4409

  Damkaci, Fehmi ^a   DeShong, Philip ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE DERIVATIVE; AZIDE; ISOXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

AMINO ACID SEQUENCE; AZIDES; GLYCOPEPTIDES; ISOXAZOLES; MOLECULAR SEQUENCE DATA; PYRANS; STEREOISOMERISM;

EID: 0037448919     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028694u     Document Type: Article

References (25)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130.
2. (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. (c) Kobata, A. Glycoconjugate J. 2000, 17, 443-464.
4. (d) Glycoproteins and Disease: Montreuil, J., Vliegenthart, J. F. G., Schachter, H., Eds.; Elsevier: Amsterdam, 1996.
5. (e) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
6. Polt, R.; Porreca, F.; Szabo, L. Z.; Bilsky, E. J.; Davis, P.; Abbruscato, T. J.; Davis, T. P.; Horvath, R.; Yamamura, H. I.; Hruby, V. J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7114-7118.
7. (a) Wieland, F.; Heitzer, R.; Schaefer, W. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5470-5474.
8. Paul, G.; Lottspeich, F.; Wieland, F. J. Biol. Chem. 1986, 261, 1020-1024.
9. (a) Shibata, S.; Miura, K. J. Biochem. 1987, 89, 1737-1749.
10. (b) Shibata, S.; Takeda, T.; Natori, Y. J. Biol. Chem. 1988, 263, 12483-12485.
11. (c) Takeda, T.; Sawaki, M.; Ogihara, Y.; Shibata, S. Chem. Pharm. Bull. 1989, 37, 54-56.
12. (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366.
13. (b) Takeda, T.; Kojima, K.; Ogihara, Y. Carbohydr. Res. 1993, 243, 79-89.
14. (c) Zhang, H.; Wang, Y.; Thürmer, R.; Al-qawasmeh, R. A.; Voelter, W. Pol. J. Chem. 1999, 73, 101-115 and references therein.
15. (d) Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1990, 112, 5665-5667.
16. (e) Nair, L. G.; Fraser-Reid, B.; Szardenings, A. K. Org. Lett. 2001, 3, 317-319 and references therein.
17. (f) Sasaki, M.; Tachibana, K. Tetrahedron Lett. 1991, 32, 6873-6876.
18. (a) Takeda, T.; Utsuno, A.; Okamoto, N.; Ogihara, Y. Carbohydr. Res. 1990, 207, 71-19.
19. (b) Zhang, H.; Wang, Y.; Thürmer, R.; Parvez, K.; Atta-ur-Rahman, I. C.; Voelter, W. Z. Naturforsch 1999, 54b, 692-698.
20. For a review on Staudinger reaction, see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406. (b) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870. (c) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106. (d) Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609-4621 and references therein.
21. For a review on Staudinger reaction, see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406. (b) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870. (c) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106. (d) Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609-4621 and references therein.
22. For a review on Staudinger reaction, see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406. (b) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870. (c) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106. (d) Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609-4621 and references therein.
23. For a review on Staudinger reaction, see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406. (b) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870. (c) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106. (d) Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609-4621 and references therein.
24. Soli, E. D.; Manoso, A. S.; Patterson, M. C.; DeShong, P.; Favor, D. A.; Hirschmann, R.; Smith, A. B. J. Org. Chem. 1999, 64, 3171-3177.
25. A listing of all acylating agents and reaction conditions investigated is summarized in the table in the Supporting Information.