Development of ketoside-type analogues of trehalose by using α-stereoselective O-glycosidation of ketose

European Journal of Organic Chemistry

Volumn , Issue 22, 2007, Pages 3758-3764

  Namme, Rie ^a   Mitsugi, Takashi ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Carbohydrates; Glycosylation; Ketose; Trehalose

Indexed keywords

EID: 34547689755     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700145     Document Type: Article

References (44)

1. A. D. Elbein, Adv. Carbohydr. Chem. Biochem. 1974, 30, 227-256.
2. a) L. M. Crowe, J. H. Crowe, Biochim. Biophys. Acta 1988, 946, 193-201;
3. b) C. Colaço, S. Sen, M. Thangarelu, S. Pinder, B. Roser, Bio-Technology 1992, 10, 1007-1011;
4. c) C. A. L. S Colaco, C. J. S. Smith, S. Sen, D. H. Roser, Y. Newman, S. Ring, B. J. Roser in Formulations and Delivery of Proteins and Peptides (Eds: J. L. Cleland, R. Langer), Symposium Series No. 567, American Chemical Society, Washington, DC, 1994, pp. 222-240.
5. K. Maruta, T. Nakada, M. Kubota, H. Chaen, T. Sugimoto, M. Kutimoto, Y. Tsujisaka, Biosci. Biotechnol. Biochem. 1995, 59, 1829-1834.
6. Selected recent reports: a) Y. Nishizaki, C. Yoshizane, Y. Toshimori, N. Arai, S. Akamatsu, S. Arai, M. Ikeda, M. Kurimoto, Nutr. Res. 2000, 20, 653-664;
7. b) M. Tanaka, Y. Machida, S. Niu, T. Ikeda, N. R. Jana, H. Doi, M. Kurosawa, N. Nukida, Nat. Med. 2004, 10, 148-154;
8. c) Y. Ukawa, Y. Gu, M. Ohtsuki, I. Suzuki, M. Hisamatsu, J. Appl. Glycosci. 2005, 52, 367-368;
9. d) K. Oku, M. Kurose, H. Chaen, S. Fukuda, Y. Tsujisaka, M. Sakurai, J. Appl. Glycosci. 2005, 52, 381-385.
10. a) J. O'Brien, J. Food Sci. 1996, 61, 679-682;
11. b) C. Scheor, L. Burin, M. Chirife Del Pilar Buera, J. Lebensm.-Wiss. Technol. 1999, 32, 481-485.
12. H. P. Wessel, T. B. Tschopp, M. Hosang, N. Iberg, Bioorg. Med. Chem. Lett. 1994, 4, 1419-1422.
13. K. Hiruma, T. Kajimoto, G. Weitz-Schmidt, I. Ollmann, C.-H. Wong, J. Am. Chem. Soc. 1996, 118, 9265-9270.
14. H. Dohi, Y. Nishida, Y. Furuta, H. Uzawa, S.-I. Yokoyama, A. Ito, H. Mori, K. Kobayashi, Org. Lett. 2002, 4, 355-357.
15. L. A. Dolak, T. M. Castle, A. L. Laborde, J. Antibiot. 1980, 33, 690-694.
16. K. Linek, J. Alföldi, J. Carbohydr. Res. 1987, 164, 195-205.
17. a) X. L. Li, H. Ohtake, H. Takahashi, S. Ikegami, Tetrahedron 2001, 57, 4283-4295;
18. b) X. L. Li, H. Ohtake, H. Takahashi, S. Ikegami, Synlett 2001, 1885-1888;
19. c) R. Namme, T. Mitsugi, H. Takahashi, S. Ikegami, Tetrahedron Lett. 2005, 46, 3033-3036;
20. d) R. Namme, T. Mitsugi, H. Takahashi, M. Shiro, S. Ikegami, Tetrahedron 2006, 62, 9183-9192.
21. a) X. L. Li, H. Ohtake, H. Takahashi, S. Ikegami, Tetrahedron 2001, 57, 4297-4309;
22. b) T. Yamanoi, Y. Oda, I. Yamazaki, M. Shinbara, K. Morimoto, S. Matsuda, Lett. Org. Chem. 2005, 2, 242-246.
23. During the preparation of this manuscript, a similar finding was published: T. Yamanoi, R. Inoue, S. Matsuda, K. Katsuraya, K. Hamasaki, Tetrahedron: Asymmetry 2006, 17, 914-2918.
24. For the synthesis of unsymmetrical 1,1-linked disaccharides, see: a) A. Klemer, E. Buhe, R. Kutz, Justus Liebigs Ann. Chem. 1970, 739, 185-193;
25. b) T. E. C. L. Ronnow, M. Meldal, K. Bock, Tetrahedron: Asymmetry 1994, 5, 2109-2122;
26. c) M. R. Pratt, C. D. Leigh, C. R. Bertozzi, Org. Lett. 2003, 5, 3185-3188.
27. For the synthesis of symmetrical 1,1-linked disaccharides, see: J. Yoshimura, K. Hara, T. Sato, H. Hashimoto, Chem. Lett. 1983, 319-320.
28. a) L.-F. Tietze, R. Fischer, H.-J. Guder, Tetrahedron Lett. 1982, 23, 4661-4664;
29. b) E. M. Nashed, C. P. J. Glaudemans, J. Org. Chem. 1989, 54, 6116-6118;
30. c) D. X. Qiu, F. Y. Wang, M. S. Cai, Synth. Commun. 1989, 19, 3453-3456;
31. d) C. Kolar, G. Kneissl, Angew. Chem. Int. Ed. Engl. 1990, 29, 809-810;
32. e) W. Priebe, G. Grynkiewicz, N. Neamati, Tetrahedron Lett. 1991, 32, 2079-2082;
33. f) T. Mukaiyama, K. Matsubara, Chem. Lett. 1992, 1041-1044;
34. g) A. Kirschning, G.-W. Chen, Tetrahedron Lett. 1999, 40, 4665-4668.
35. A. J. Kirby, Acc. Chem. Res. 1984, 17, 305-311.
36. For some reports concerning the α-selective C-glycosidation with an oxocarbenium ion intermediate, see: a) M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 4976-4978;
37. b) S. A. Babirad, Y. Wang, Y. Kishi, J. Org. Chem. 1987, 52, 1370-1372;
38. c) C. G. Lucero, K. A. Woerpel, J. Org. Chem. 2006, 71, 2641-2647, and references cited therein.
39. L. E. Tietz, R. Fischer, H. J. Guder, A. Goerlach, M. Newmann, T. Krach, Carbohydr. Res. 1987, 164, 177-194.
40. L.-F. Tietze, R. Fischer, H.-J. Guder, Synthesis 1982, 946-948.
41. [14a]
42. a) H. H. Jensen, M. Bols, Org. Lett. 2003, 5, 3419-3421;
43. b) M. Miljkovic, D. Yeagley, P. Deslongchamps, S. Li, Y. L. Dory, J. Org. Chem. 1997, 62, 7497-7604.
44. For the spectroscopic data of all synthesized disaccharides, see the Supporting Information.