An efficient synthesis of N-allylglycosylamides from unprotected carbohydrates

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3417-3422

  Spevak, Wayne ^a   Dasgupta, Falguni ^a   Hobbs, Christopher J ^a   Nagy, Jon O ^a  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029974381     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522522     Document Type: Article

References (34)

1. Sharon, N. TIBS 1993, 18, 221.
2. Bullough, P. A.; Hughson, F. M.; Skehel, J. J.; Wiley, D. C. Nature 1994, 371, 37.
3. Weis, W. I.; Quesenberry, M. S.; Taylor, M. E.; Bezouska, K.; Hendrickson, W. A.; Drickamer, K. Cold Spring Harbor Symp Quant. Biol. 1992, 57, 281.
4. Barondes, S. H.; Gitt, M. A.; Leffler, H.; Cooper, D. N. W. Biochimie 1988, 70, 1627.
5. Oda, S.; Sato, M.; Toyoshima, S.; Osawa, T. J. Biochem. 1988, 104, 600.
6. Harlan, J. M., Liu, D. Y., Eds. Adhesion: Its Role in Inflammatory Disease; W. H. Freeman: New York, 1992.
7. Bezouska, K.; Yuen, C-T.; O'Brien, J.; Childs, R. A ; Chai W.; Lawson, A. M.; Drbal, K ; Fiserova, A.; Pospisil, M.; Feizi, T. Nature 1994, 372, 150.
8. Constantin, G.; Laudanna, C., Baron, P.; Berton, G. FEBS Lett. 1994, 350, 66.
9. Lee, Y. C., Lee, R. T Eds. Neoglycoconjugates, Preparation and Application: Academic Press: San Diego, 1994; pp 23-50.
10. Lockhoff, O. Angew. Chem., Int. Ed. Engl. 1991, 30, 1611.
11. Paulsen, H.; Györgydeak, Z.; Friedmann, M. Chem. Ber. 1974, 107, 1590.
12. Tsujihara, K.; Ozeki, M.; Morikawa, T.; Kawamori, M.; Akaike, Y.; Arai, Y. J. Med. Chem. 1982, 25, 441.
13. Tsujihara, K.; Ozeki, M.; Morikawa, T.; Taga, N.; Miyazaki, M.; Kawamori, M.; Arai, Y. Chem. Pharm. Bull. 1981, 29, 3262.
14. Morikawa, T.; Ozeki, M.; Umino, N.; Kawamori, M.; Arai, Y.; Tsujihara, K. Chem. Pharm. Bull. 1982, 30, 534.
15. Nicolaou, K. C.; Chucholowski, A.; Dolle, R. E.; Randall, J. L. J. Chem. Soc., Chem. Commun. 1984, 1155.
16. Vigdorchik, M. M.; Kostyuchenko, N. P.; Olad'ko, R P.; Mosina, G. S.; Sheinker, Yu.N.; Suvorov, N. L. J. Org. Chem. USSR (Engl. Transl.) 1973, 9, 617.
17. Banishefsky, S. J.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Koseki, K.; Griffith, D. A., Oriyama, T Marsden, S. P. J. Am. Chem. Soc. 1995, 117, 1940.
18. Peters, S.; Bielfeldt, T.; Meldal, M.; Bock, K.; Paulsen, H. J. Chem Soc., Perkin Trans. 1 1992, 1163.
19. Roy, R.; Tropper, F. D. J. Chem. Soc., Chem. Commun. 1988, 1058.
20. Roy, R.; Laferriere, C. A. Carbohydr. Res. 1988, 177, C1.
21. Allanson, N. M.; Davidson, A. H.; Martin, F. M. Tetrahedron Lett. 1993, 34, 3945.
22. Kallin, E.; Lönn, H.; Norberg, T.; Elofsson, M. J. Carbohydr. Chem. 1989, 8, 597.
23. Spevak, W.; Nagy, J. O.; Tropper, F. D. Manuscript in preparation.
24. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155.
25. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
26. Mieheel, F.; Köchling, H. Chem. Ber. 1957, 90, 1597.
27. Hodge, J. E.; Moy, B. F. J Org. Chem. 1963, 28, 2784.
28. Likhosherstov, L. M.; Novikova, O. S.; Derevitskaja, V A.; Kochetkov, N. K. Carbohydr. Res. 1986, 146, C1.
29. Isbell, H. S.; Frush, H. L. J Org. Chem. 1958, 23, 1309.
30. Lubineau, A.; Augé, J.; Drouillat, B. Carbohydr. Res. 1995, 266, 211.
31. Vetter, D.; Gallop, M. A. Bioconjugate Chem. 1995, 6, 316.
32. Dasgupta, F.; Rao, B. N. N. Exp. Opin. Invest. Drugs 1994, 3, 709.
33. Spevak, W.; Foxall, C.; Charych, D H.; Dasgupta, F.; Nagy, J. O. J. Med. Chem. 1996, 39, 1018.
34. Osawa, T.; Nakazawa, Y. Biochim. Biophys. Acta 1966, 130, 56.