First synthesis of a branched β-C-tetrasaccharide using a triple ring closing metathesis cyclization

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7395-7398

  Piper, Jared L ^a,b   Postema, Maarten H D ^a,c  

^a WAYNE STATE UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c HENRY FORD HEALTH SYSTEM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL ANALYSIS; DEHYDRATION; ESTERIFICATION; OLEFINS; OXIDATION; SYNTHESIS (CHEMICAL);

DEHYDRATIVE COUPLING; ESTERIFICATION-RING CLOSING METATHESIS (RCM); HYDROBORATION-OXIDATION;

POLYSACCHARIDES;

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CYCLIZATION; ESTERIFICATION; HYDROBORATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CYCLIZATION; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 5444252717     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040203w     Document Type: Article

References (40)

1. Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491-514.
2. Sasisekharan, R.; Myette, J. R. Am. Sci. 2003, 91, 432-441.
3. Perkel, J. M. Scientist 2002, 19, 32-34.
4. Nagai, Y. Glycoconjuguate J. 2002, 19, 161-163.
5. Roseman, S. J. Biol. Chem. 2001, 276, 41527-41542.
6. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
7. Postema, M. H. D.; Calimente, D. In Glycochemistry: Principles, Synthesis and Applications; Wang, P. G., Bertozzi, C., Eds.; Marcel Dekker: New York, 2000; pp 7-131.
8. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959.
9. Postema, M. H. D. C-Glycoside Synthesis, 1st ed.; CRC Press: Boca Raton, 1995; p 379.
10. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides, 1st ed.; Elsevier Science: Oxford, 1995; Vol. 13, p 291.
11. Postema, M. H. D.; Calimente, D. J. Org. Chem. 1999, 64, 4, 1770-1771.
12. Postema, M. H. D.; Piper, J. L. Org. Lett. 2003, 5, 1721-1723.
13. Postema, M. H. D.; Chaulagain, M. R. Tetrahedron Lett. 2004, 45, in press.
14. Postema, M. H. D.; Calimente, D.; Liu, L.; Behrmann, T. L. J. Org. Chem. 2000, 65, 6061-6068.
15. Postema, M. H. D.; Piper, J. L.; Liu, L.; Faust, M.; Andreana, P. J. Org. Chem. 2003, 68, 4748-4754.
16. Postema, M. H. D.; Piper, J. L.; Komanduri, V.; Liu, L. Angew. Chem., Int. Ed. Engl. 2004, 43, 2915-2918.
17. For examples of double and polycyclization RCM reactions, see: (a) Grubbs, R. H.; Fu, G. C. J. Am. Chem. Soc. 1992, 114, 7324-7325.
18. (b) Wallace, D. J.; Bulger, P. G.; Kennedy, D. J.; Ashwood, M. S.; Cottrell, I. F.; Dolling, U.-H. Synlett 2001, 3, 357-360.
19. (c) Wallace, D. J.; Cowden, C. J.; Kennedy, D. J.; Ashwood, M. S.; Cottrell, I. F.; Dolling, U.-H. Tetrahedron Lett. 2000, 41, 2027-2029.
20. (d) Schmidt, B.; Wildemann, H. J. Chem. Soc., Perkin Trans, 1 2000, 2916-2925.
21. (e) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372-374.
22. (f) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298.
23. Liu, L.; McKee, M.; Postema, M. H. D. Curr. Org. Chem. 2001, 5, 1133-1167.
24. Dondoni, A.; Marra, A.; Mizuno, M.; Giovannini, P. P. J. Org. Chem. 2002, 67, 4186-4199.
25. Xin, Y.-C.; Zhang, Y.-M.; Mallet, J.-M.; Glaudemans, C. P. J.; Sinay, P. Eur. J. Org. Chem. 1999, 471-476.
26. For examples of enol ether-olefin metathesis reactions, see: (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566.
27. (b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
28. (c) Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126.
29. (d) Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310-5311.
30. (e) Sturino, C. F.; Wong, J. C. Y. Tetrahedron Lett. 1998, 39, 9623-9626.
31. (f) Oishi, T.; Nagumo, Y.; Shoji, M.; Le Brazidec, J.-Y.; Uehara, H.; Hirama, M. J. Chem. Soc., Chem. Commun. 1999, 2035-2036.
32. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
33. Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386.
34. Pappo, R.; Allen, D., Jr.; Lemieux, R.; Johnson, W. J. Org. Chem. 1956, 21, 478-479.
35. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
36. Freeman, F.; Robarge, K. D. Carbohydr. Res. 1987, 171, 1-11.
37. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670.
38. Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927.
39. Schmidt, R. R.; Preuss, R.; Betz, R. Tetrahedron Lett. 1987, 28, 6591-6594.
40. See Supporting Information.