Stereoselective glycosylation based on the conformational restriction of pyranoses

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 66, Issue 1, 2008, Pages 50-59

  Shuto, Satoshi ^a   Ichikawa, Satoshi ^b   Abe, Hiroshi ^b   Matsuda, Akira ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b NONE

Author keywords

Anomeric effect; C glycosides; Conformational restriction; Glycosylation; Radical reaction; Silicon tether

Indexed keywords

GLYCOSYLATION; STEREOSELECTIVITY; TETHERLINES;

ANOMERIC EFFECT; CONFORMATIONAL RESTRICTION; RADICAL REACTION; SILICON TETHER;

AROMATIC COMPOUNDS;

EID: 42149136186     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.66.50     Document Type: Article

References (42)

1. (a) A. V. Demchenko, Synlett, 2003, 1225;
2. (b) J. J. Gridley, H. M. I. Osborn, J. Chem. Soc., Perkin Trans 1, 2000, 1471
3. (a) D. E. Leavy, C. Tang, "The Chemistry of C- Glycosides", Pergamon, Oxford press, 1995;
4. (b) M. H. D. Postema, "C-Glycoside Synthesis", CRC, press Boca Raton, 1995
5. (a) S. Ichikawa, S. Shuto, A. Matsuda, Tetrahedron Lett., 39, 4525 (1998);
6. (b) idem, J. Am. Chem. Soc., 121, 10270 (1999)
7. (a) H. Abe, S. Shuto, A. Matsuda, J. Org. Chem., 65, 4315 (2000);
8. (b) idem, Tetrahedron Lett., 41, 2391 (2000)
9. (a) Y. Yahiro, S. Ichikawa, S. Shuto, A. Matsuda, Tetrahedron Lett., 40, 5527 (1999);
10. (b) S. Shuto, Y. Yahiro, S. Ichikawa, A. Matsuda, J. Org. Chem., 65, 5547 (2000)
11. (a) H. Abe, S. Shuto, A. Matsuda, J. Am. Chem. Soc., 123, 11870 (2001);
12. (b) H. Abe, S. Shuto, S. Tamura, A. Matsuda, Tetrahedron Lett., 42, 6159 (2001);
13. (c) H. Abe, M. Terauchi, A. Matsuda, S. Shuto, J. Org. Chem., 68, 7439 (2003)
14. S. Tamura, H. Abe, A. Matsuda, S. Shuto, Angew. Chem. Int. Ed., 42, 1021 (2003)
15. (a) S. Shuto, M. Terauchi, Y. Yahiro, H. Abe, S. Ichikawa, A. Matsuda, Tetrahedron Lett., 41, 4151 (2000);
16. (b) M. Terauchi, Y. Yahiro, H. Abe, S. Ichikawa, S. C. Tovey, S. G. Dedos, C. W. Taylor, B. V. L. Potter, A. Matsuda, S. Shuto, Tetrahedron, 61, 3697 (2005);
17. (c) M. Terauchi, A. Matsuda, S. Shuto, Tetrahedron Lett., 46, 6555 (2005)
18. M. Terauchi, H. Abe, A. Matsuda, S. Shuto, Org. Lett., 6, 3751 (2004)
19. M. Terauchi, H. Abe, S. C. Tovey, S. G. Dedos, C. W. Taylor, M. Paul, M. Trusselle, B. V. L. Potter, A. Matsuda, S. Shuto, J. Med. Chem., 49, 1900 (2006)
20. (a) E. Juaristi, G. Cuevas, Tetrahedron, 48, 5019 (1992);
21. (b) "The Anomeric Effect and Associated Stereoelectronic Effects" ed. by G. R. J. Thatche, ACS Symposium Series 539, American Chemical Society, Washington DC, 1993;
22. (c) E. Juaristi, G. Cuevas, "The Anomiric Effect", CRC Press, Boca Raton, 1995
23. (a) A. M. Tius, J. Bushe-Petersen, Tetrahedron Lett., 35, 5181 (1994);
24. (b) T. Hosoya, Y. Ohashi, T. Matsumoto, K. Suzuki, ibid., 37, 663 (1996)
25. T. Matsumoto, M. Katsuki, K. Suzuki, Tetrahedron Lett., 30, 833 (1989)
26. (a) T. Mochizuki, Y. Kondo, H. Abe, C. W. Taylor, B. L. V. Potter, A. Matsuda, S. Shuto, Org. Lett., 8, 1455 (2006);
27. (b) T. Mochizuki, Y. Kondo, H. Abe, S. C. Tovey, S. G. Dedos, C. W. Taylor, M. Paul, B. V. L. Potter, A. Matsuda, S. Shuto, J. Med. Chem., 49, 5750 (2006)
28. R. W. Frank, "Conformational behavior of six-membered rings" ed. by E. Juaristi, VCH publisher, 1995, New York, p159-200
29. (a) M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc., 104, 4976 (1982);
30. (b) Y. Wang, S. A. Babirad, Y. Kishi, J. Org. Chem., 57, 468 (1992)
31. (a) D. Crick, S. Sun, J. Am. Chem. Soc., 119, 11217 (1997);
32. (b) D. Crich, H. Xu, J. Org. Chem., 72, 5183 (2007)
33. (a) K. Toshima, S. Mukaiyama, Y. Nozaki, H. Inokuchi, M. Nakata, K. Tatsuta, J. Am. Chem. Soc., 116, 9042 (1994);
34. (b) Y. Okada, T. Mukae, K. Okajima, M. Taira, M. Fujita, H. Yamada, Org. Lett., 9, 1573 (2007)
35. (a) S. Shuto, M. Kanazaki, S. Ichikawa, A. Matsuda, J. Org. Chem., 62, 5676 (1997);
36. (b) S. Sugimoto, S. Shuto, A. Matsuda, ibid., 64, 7153 (1999);
37. (c) S. Shuto, I. Sugimoto, H. Abe, A. Matsuda, J. Am. Chem. Soc., 122, 1343 (2000);
38. (d) M. Sukeda, S. Ichikawa, A. Matsuda, S. Shuto, Angew. Chem. Int. Ed., 41, 4748 (2002)
39. G. Stork, H. S. Suh, G. Kim, J. Am. Chem. Soc., 113, 7054 (1991)
40. (a) Z. Xi, P. Agback, J. Plavec, A. Sandström, J. Chattopadhyaya, Tetrahedron, 48, 349 (1992);
41. (b) M. Kanazaki, Y. Ueno, S. Shuto, A. Matsuda, J. Am. Chem. Soc., 122, 2422 (2000)
42. T. Nukada, A. Berces, L. Wang, M. Z. Zgierski, D. M. Whitfield, Carbohydr. Res., 340, 841 (2005)