Synthetic study on α(2→8)-linked oligosialic acid employing 1,5-lactamization as a key step

Tetrahedron Letters

Volumn 50, Issue 31, 2009, Pages 4478-4481

  Tanaka, Hidenori ^a   Ando, Hiromune ^a,b   Ishida, Hideharu ^a   Kiso, Makoto ^a,b   Ishihara, Hideharu ^a   Koketsu, Mamoru ^a  

^a GIFU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Glycosylation; Lactam; Oligosialic acid; Sialic acid

Indexed keywords

SIALIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SIALYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 66949160801     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.057     Document Type: Article

References (34)

1. Angata T., and Varki A. Chem. Rev. 102 (2002) 439-470
2. Varki A. Nature 446 (2007) 1023-1029
3. Murrey H.E., and Hsieh-Wilson L.C. Chem. Rev. 108 (2008) 1708-1731
4. Daniloff J.K., Chuong C.-M., Levi G., and Edelman G.M. J. Neurosci. 6 (1986) 739-758
5. Svennerholm L., Boström K., Fredman P., Månsson J.-E., Rosengren B., and Rynmark B.-M. Biochim. Biophys. Acta 1005 (1989) 109-117
6. Tsuji S., Arita M., and Nagai Y. J. Biochem. 94 (1983) 303-306
7. Indirect method:. Okamoto K., Kondo T., and Goto T. Tetrahedron Lett. 27 (1986) 5229-5232
8. Ito Y., Numata M., Sugimoto M., and Ogawa T. J. Am. Chem. Soc. 111 (1989) 8508-8510
9. Castro-Palomino J.C., Tsvetkov Y.E., and Schmidt R.R. J. Am. Chem. Soc. 120 (1998) 5434-5440
10. Hossain N., and Magnusson G. Tetrahedron Lett. 40 (1999) 2217-2220
11. Direct method:. De Meo C., Demchenko A.V., and Boons G.-J. J. Org. Chem. 66 (2001) 5490-5497
12. Ando H., Koike Y., Koizumi S., Ishida H., and Kiso M. Angew. Chem., Int. Ed. 44 (2005) 6759-6763
13. Tanaka H., Nishiura Y., Adachi M., and Takahashi T. Heterocycles 67 (2006) 107-112
14. Tanaka H., Nishiura Y., and Takahashi T. J. Am. Chem. Soc. 128 (2006) 7124-7125
15. Tsvetkov Y.E., and Schmidt R.R. Tetrahedron Lett 35 (1994) 8583-8586
16. Boons G.-J., and Demchenko A.V. Chem. Rev. 100 (2000) 4539-4566
17. Marra A., and Sinaÿ P. Carbohydr. Res. 187 (1989) 35-42
18. Cai S., and Yu B. Org. Lett. 5 (2003) 3827-3830
19. Komba S., Galustian C., Ishida H., Feizi T., Kannagi R., and Kiso M. Angew. Chem., Int. Ed. 38 (1999) 1131-1133
20. Matsuoka K., Oka H., Terunuma D., and Kuzuhara H. Carbohydr. Lett. 4 (2001) 123-130
21. Bayley H., Standring D.N., and Knowles J.R. Tetrahedron Lett. 39 (1978) 3633-3634
22. Veeneman G.H., van Leeuwen S.H., and van Boom J.H. Tetrahedron Lett. 31 (1990) 1331-1334
23. Konradsson P., Udodong U.E., and Fraser-Reid B. Tetrahedron Lett. 31 (1990) 4313-4316
24. Schmidt R.R., and Rücker E. Tetrahedron Lett. 21 (1980) 1421-1424
25. Hashimoto S., Hayashi M., and Noyori R. Tetrahedron Lett. 25 (1984) 1379-1382
26. Kanie O., Kiso M., and Hasegawa A. J. Carbohydr. Chem. 7 (1988) 501-506
27. Hasegawa A., Nagahama T., Ohki H., Hotta K., Ishida H., and Kiso M. J. Carbohydr. Chem. 10 (1991) 493-498
28. In the carbodiimide-mediated lactamization, β-sialoside was converted into the corresponding N-acylurea derivative.
29. See the Supplementary data.
30. Hori H., Nakajima T., Nishida Y., Ohrui H., and Meguro H. Tetrahedron Lett. 29 (1988) 6317-6320
31. Haverkamp J., Spoormaker T., Dorland L., Vliegenthart F.G., and Schauer R. J. Am. Chem. Soc. 101 (1979) 4851-4853
32. Prytulla S., Lauterwein J., Klessinger M., and Thiem J. Carbohydr. Res. 215 (1991) 345-349
33. Ito Y., and Ogawa T. Tetrahedron Lett. 29 (1988) 1061-1064
34. Crich D., and Li W. Org. Lett. 8 (2006) 959-962