Palladium-Charcoal-Catalyzed Reduction of Tri-O-acetyl-β-L-Fucopyranosyl Cyanide: A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4587-4590

  Phiasivongsa, Pasit ^a   Gallagher, Julie ^a   Chen, Chang Nan ^a   Jones, Patrick R ^a   Samoshin, Vyacheslav V ^a   Gross, Paul H ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARCOAL; CYANIDE; FUCOSE; OLIGOSACCHARIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; MOLECULAR MIMICRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; CHARCOAL; CYANIDES; FUCOSE; MOLECULAR MIMICRY; OLIGOSACCHARIDES; OXIDATION-REDUCTION; PALLADIUM;

EID: 0442265713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020123j     Document Type: Article

References (28)

1. (a) Kishi, Y. Pure Appl. Chem. 1989, 61, 313.
2. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Elsevier Science, Ltd.: Oxford, U.K., 1995; p 4.
3. (a) Fritz, H.; Lehman, J.; Schlesselman, P. Carbohydr. Res. 1983, 113, 71.
4. (b) Gross, P. H. Carbohydr. Polym. 1998, 37, 215.
5. Helferich, B.; Bettin, K. L. Chem. Ber. 1961, 94, 1159.
6. (a) Coxon, B.; Fletcher, H. G., Jr. J. Am. Chem. Soc., 1963, 85, 2637.
7. (b) Coxon, B.; Fletcher, H. G., Jr. J. Am. Chem. Soc., 1964, 86, 922.
8. (c) Coxon, B.; Hall, L. D. Tetrahedron 1964, 20, 1685.
9. (d) Coxon, B. Ann. NY Acad. Sci. 1973, 952.
10. Myers, R. W.; Lee, Y. C. Carbohydr. Res. 1984, 132, 61; Carbohydr. Res. 1986, 154, 145.
11. Myers, R. W.; Lee, Y. C. Carbohydr. Res. 1984, 132, 61; Carbohydr. Res. 1986, 154, 145.
12. De Las Heras, F. G.; Fernandez-Resa, P. J. Chem. Soc., Perkin Trans. 1982, 1, 903.
13. (a) Utimoto, K.; Horiie, T. Tetrahedron Lett., 1982, 23, 237.
14. (b) Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron, 1983, 39, 967.
15. (a) Phiasivongsa, P. Ph.D. Dissertation, University of the Pacific, Stockton, CA, 2002.
16. (b) Phiasivongsa, P.; Samoshin, V. V.; Gross, P. H. XXIst International Carbohydrate Symposium, July 7-12, 2002, Cairns, Australia: Abstracts PP225 and PP226.
17. Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1979, 68, C11.
18. Kini, G. D.; Petrie, C. R.; Hennen, W. J.; Dalley, N. K.; Wilson, B. E.; Robins, R. K. Carbohydr. Res., 1987, 159, 81.
19. Franz, A. Ph.D. Dissertation, University of the Pacific, Stockton, CA, 2000. Franz, A. et al. J. Org. Chem. In press.
20. Franz, A. Ph.D. Dissertation, University of the Pacific, Stockton, CA, 2000. Franz, A. et al. J. Org. Chem. In press.
21. Vicent, C.; Coteron, J.-M.; Jimenez-Barbero, J.; Martin-Lomas, M.; Penades, S. Carbohydr. Res. 1989, 194, 163.
22. Gallagher, J. M.S. Thesis, University of the Pacific, Stockton, CA, 1989.
23. Brieger, G.; Nestrick, T. J. Chem. Rev. 1974, 74, 567.
24. Gross, P. H.; Phiasivongsa, P. 219th National Meeting of the American Chemical Society, San Francisco, CA, 2000, Division of Carbohydrate Chemistry; American Chemical Society: Washington, DC, 2000; Abstract 36.
25. Lentz, D. H.; Norris, G. E.; Taylor, C. M.; Slim, G. C. Tetrahedron Lett. 2001, 42, 4589.
26. Iwakura, Y.; Uno, K. J. Org. Chem. 1965, 30, 1158.
27. Gnichtel, H.; Rebentisch, D.; Tompkins, T. C.; Gross, P. H. J. Org. Chem. 1982, 47, 2691.
28. 4 (173.17): C, 48.55; H, 6.40; N, 8.09. Found: C, 48.48; H, 6.70; N, 8.01.