Regiospecific glycosidation of unprotected sugars via arylboronic activation [5]

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2315-2316

  Oshima, Kenji ^a   Aoyama, Yasuhiro ^b  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; GALACTOSIDE; MANNOSIDE; OLIGOSACCHARIDE;

CHEMICAL STRUCTURE; COMPLEX FORMATION; GLYCOSYLATION; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0033577276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982395g     Document Type: Letter

References (28)

1. (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-175; 1990, 29, 823-839.
2. (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-175; 1990, 29, 823-839.
3. (b) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235.
4. (c) Garegg, P. J. Acc. Chem. Res. 1992, 25, 575-580.
5. (d) Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167-1195.
6. (e) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
7. (f) Boons, G. J. Tetrahedron 1996, 52, 1095-1121.
8. Tsuda, Y. J. Synth. Org. Chem. Jpn. 1997, 55, 907-919.
9. (a) Ogawa, T.; Matsui, M. Carbohydr. Res. 1978, 62, C1-4.
10. (b) David, S.; Thieffry, A.; Veyrières, A. J. Chem. Soc., Perkin Trans. 1 1981, 1796-1801.
11. (a) Nashed, M. A.; Anderson, L. Tetrahedron Lett. 1976, 3503-3506.
12. (b) Tsuda, Y.; Haque, M. D.; Yoshimoto, K. Chem. Pharm. Bull. 1983, 31, 1612-1624.
13. Lubineau, A.; Lemoine, R. Tetrahedron Lett. 1994, 35, 8795-8796.
14. (a) Nicolaou, K. C.; van Delft, F. L.; Conley, S. R.; Mitchell, H. J.; Jin, Z.; Rodriguez, R. M. J. Am. Chem. Soc. 1997, 119, 9057-9058 and references therein.
15. (b) For the ortho ester formation from unprotected sugars, see: Ogawa, T.; Katano, K.; Matsui, M. Carbohydr. Res. 1978, 64, C3-9.
16. Oshima, K.; Kitazono, E.; Aoyama, Y. Tetrahedron Lett. 1997, 38, 5001-5004.
17. (a) Ferrier, R. J. J. Chem. Soc. 1961, 2325-2330.
18. (b) Ferrier, R. J.; Prasad, D.; Rudowski, A.; Sangster, I. J. Chem. Soc. 1964, 3330-3334.
19. (c) Huttunen, E. Ann. Acad. Sci. Fenn. Ser. A2 1984, 201, 1-45.
20. (d) Verchere, J. F.; Hlaibi, M. Polyhedron 1987, 6, 1415-1420.
21. (e) Kondo, K.; Shiomi, Y.; Saisho, M.; Harada, T.; Shinkai, S. Tetrahedron 1992, 48, 8239-8252.
22. (f) Oshima, K.; Toi, H.; Aoyama, Y. Carbohydr. Lett. 1995, 1, 223-230.
23. Ferrier, R. J.; Prasad, D. J. Chem. Soc. 1965, 7429-7432.
24. 13C COSY spectra.
25. 3 species, respectively.
26. Brown, A. G., Grimmin, M. J.; Edwards, P. D. J. Chem. Soc., Perkin Trans. 1 1992, 123-130.
27. Lauer, M.; Wulff, G. J. Organomet. Chem. 1983, 256, 1-9.
28. + to give ortho ester 12b.