Iodoamidation of glycals: A facile preparation of 2-deoxy-N-glycosylamides

ACS Symposium Series

Volumn 960, Issue , 2007, Pages 50-58

  Marzabadi, Cecilia H ^a   DeCastro, Michael ^a  

^a SETON HALL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36849001758     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2007-0960.ch004     Document Type: Conference Paper

References (36)

1. Varki, A. Glycobiology 1993, 3, 97.
2. Lockoff, O.; Stadler, P. Carbohydr. Res. 1998, 314, 13-24.
3. Davis, B. Chem. Rev. 2002, 102, 579-601.
4. Pleuss, N.; Kunz, H. Synthesis 2005, 122-130.
5. Rottmann, A.; Synstad, B.; Eijsink, V.; Peter, M. Eur. J. Org. Chem. 1999, 2293-2297.
6. Balakrishnan, V.; Gilbert, N. E.; Brueggemeier, R. W.; Curley, R. W. Bioorg. Med. Chem. Lett. 1997, 7, 3033-3038.
7. Abell, A. D.; Blunt, J. W.; Foulds, G. J.; Munro, M. H. G. J. Chem. Soc., Perkin Trans. I, 1997, 1647.
8. Murphy, P. V.; Pitt, N.; O'Brien, A.; Enright, P. M.; Dunne, A.; Wilson, S. J.; Duane, R. M.; O'Boyle, K. M. Bioorg. Med. Chem. Lett. 2002, 12, 3287-3290.
9. Kassab, R.; Felix, C.; Parrot-Lopez, H.; Bonaly, R. Tetrahedron Lett. 1997, 38, 7555.
10. Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106.
11. Carbohydrate Chemistry. Monosaccharides, Disaccharides and Specific Oligosaccharides; Royal Society of Chemistry 2000, Vol. 31, Ch. 10, 142-157.
12. For example see: Lubineau, A.; Auge, J.; Drouillat, B. Carbohydr. Res. 1995, 266, 211-219.
13. Simo, O.; Lee, V. P.; Davis, A. S.; Kreutz, C.; Gross, P. H.; Jones, P. R.; Michael, K. Carbohydr. Res. 2005, 340, 557-566.
14. a) Bianchi, A.; Russo, A.; Bernardi, A. Tetrahedron: Assymetry 2005, 16, 381-386.;
15. b) Sabesan, S. Tetrahedron Lett. 1997, 38, 3127-3130.
16. Kovacs, L.; Osz, E.; Domokos, V.; Holzer, W.; Gyorgydeak, Z. Tetrahedron 2001, 57, 4609-4621.
17. Root, Y.; Bailor, M.; Norris, P. Syn. Commun. 2004, 34, 2499-2506.
18. Gunther, W.; Kunz, H. Angew. Chem. Int. Ed. Engl. 1990, 29, 1050.
19. Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796.
20. Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881.
21. a) Shibata, S.; Miyagawa, Y.; Naruse, T.; Takuma, T. J. Immunol. 1969, 102, 593.;
22. b) Shibata, S.; Nagasawa, T. J. Immunol. 1971, 106, 1284.
23. Laupichler, L.; Sowa, C. E.; Thiem, J. Bioorg. & Med. Chem. 1994. 2, 1281-1294.
24. Reddy, B. G.; Madhusudanan, K. P.; Vankar, Y. D. J. Org. Chem. 2004, 69, 2630-2633.
25. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
26. Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696.
27. Roush, W. R.; Briner, K.; Sebesta, D. P. Synlett 1993, 264-265.
28. a) Kessler, H.; Kottenhahn, M.; Kling, A.; Kolar, C. Angew. Chem. Int. Ed. Engl. 1987, 888-890.;
29. b) Kottenhahn, M.; Kessler, H. Liebigs Ann. Chem. 1991, 727-744.
30. Marzabadi, C.; Spilling, C. D. J. Org. Chem. 1993, 58, 3761-3766.
31. Laupichler, L.; Thiem, J. Synlett 1992, 159.
32. Isac-Garcia, J.; Hernandez-Mateo, F.; Calvo-Flores, F.; Santoyo-Gonzalez, F. J. Org. Chem. 2004, 69, 202-205.
33. Griffith, D.; Danishefsky, S. J. Am. Chem. Soc. 1990, 112, 5811-5819.
34. Thiem, J.; Klaffke, W. Top. in Curr. Chem. 1990, 154, 285-333.
35. DeCastro, M.; Marzabadi, C. H. Tetrahedron Lett. 2004, 45, 6501-6504.
36. DeCastro, M; Marzabadi, C. H. J. Carbohydr. Chem. 2005, 24, 179-185.