Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides

Tetrahedron Asymmetry

Volumn 20, Issue 6-8, 2009, Pages 781-794

  Hagena, Tara L ^a   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 FLUORO LACTOSAMINE; ACETIC ACID DERIVATIVE; ALKENE; BENZENE DERIVATIVE; BETA 1,3 DISACCHARIDE; BETA 1,4 DISACCHARIDE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; EPOXIDE; FLUORINE; FUCOSYLTRANSFERASE; GLYCAN; GLYCOSIDE; HEXAMETHONIUM BROMIDE; HYDROXYL GROUP; ISOLACTOSAMINE GLYCOSIDE; LEWIS ACID; OLIGOSACCHARIDE; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; HUMAN; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; SYNTHESIS; THERMAL EXPOSURE;

EID: 65549144610     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.03.025     Document Type: Article

References (22)

1. Williams S.J., and Withers S.G. Carbohydr. Res. 327 (2000) 27-48
2. Rempel B.P., and Withers S.G. Glycobiology 18 (2008) 570-586
3. Lairson L.L., Henrissat B., Davies G.J., and Withers S.G. Ann. Rev. Biochem. 77 (2008) 521-555
4. Timperley C.M., and White W.E. J. Fluorine Chem. 123 (2003) 65-70
5. Richard J.P., Heo C.K., and Toteva M.M. J. Phys. Org. Chem. 21 (2008) 531-537
6. Vocadlo D.J., Mayer C., He S.M., and Withers S.G. Biochemistry 39 (2000) 117-126
7. Somsak L., and Ferrier R.J. Adv. Carbohydr. Chem. Biochem. 49 (1991) 37-92
8. Stubbs K.A., Scaffidi A., Debowski A.W., Mark B.L., Stick R.V., and Vocadlo D.J. J. Am. Chem. Soc. 130 (2008) 327-335
9. Hartman M.C.T., and Coward J.K. J. Am. Chem. Soc. 124 (2002) 10036-10053
10. Hartman M.C.T., Jiang S., Rush J.S., Waechter C.J., and Coward J.K. Biochemistry 46 (2007) 11630-11638
11. Sun H.-Y., Lin S.-W., Ko T.-P., Pan J.-F., Liu C.-L., Lin C.-N., Wang A.H.-J., and Lin C.-H. J. Biol. Chem. 282 (2007) 9973-9982
12. Homeister J.W., Thall A.D., Petryniak B., Maly P., Rogers C.E., Smith P.L., Kelly R.J., Gersten K.M., Askari S.W., Cheng G.Y., Smithson G., Marks R.M., Misra A.K., Hindsgaul O., von Andrian U.H., and Lowe J.B. Immunity 15 (2001) 115-126
13. Palcic M.M., Heerze L.D., Pierce M., and Hindsgaul O. Glycoconjugate J. 5 (1988) 49-63
14. Barresi F., and Hindsgaul O. Can. J. Chem. 72 (1994) 1447
15. Fort S., Kim H.S., and Hindsgaul O. J. Org. Chem. 71 (2006) 7146-7154
16. Ding Y.L., Fukuda M., and Hindsgaul O. Bioorg. Med. Chem. Lett. 8 (1998) 1903-1908
17. Crich D., and Dudkin V. J. Am. Chem. Soc. 123 (2001) 6819-6825
18. Hagena, T. L., Ph.D. Thesis, University of Michigan, 2008.
19. Grieco P.A., Jaw J.Y., Claremon D.A., and Nicolaou K.C. J. Org. Chem. 46 (1981) 1215-1217
20. Witczak Z.J., and Czernecki S. Adv. Carbohydr. Chem. Biochem. 53 (1998) 143-199
21. Murray R.W., and Singh M. Org. Synth. IX (1998) 288-293
22. Bukowski R., Morris L.M., Woods R.J., and Weimar T. Eur. J. Org. Chem. (2001) 2697-2705