Studies on the selectivity between glycosylation and intermolecular aglycone transfer of thioglucoside in synthesis of lactose derivatives

Chemistry Letters

Volumn 40, Issue 8, 2011, Pages 877-879

  Kato, Marie ^a,b   Hirai, Go ^a   Sodeoka, Mikiko ^a,b,c  

^a RIKEN   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84866081344     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.877     Document Type: Article

References (37)

1. a) G.-J. Boons, in Glycoscience: Chemistry and Chemical Biology, ed. by B. Fraser-Reid, K. Tatsuta, J. Thiem, Springer-Verlag Berlin Heidelberg, 2001, Vol. 1, Chap. 3.3.2, pp. 551581.
2. b) W. Zhong, G.-J. Boons, D. Crich, A. A. Bowers, W. Szeja, G. Grynkiewicz, in Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance, ed. by A. V. Demchenko, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008, Chap. 4, pp. 261361.
3. K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503.
4. Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734.
5. a) J. Kihlberg, E. Eichler, D. R. Bundle, Carbohydr. Res. 1991, 211, 59.
6. b) S. Knapp, S. R. Nandan, J. Org. Chem. 1994, 59, 281.
7. c) D. A. Leigh, J. P. Smart, A. M. Truscello, Carbohydr. Res. 1995, 276, 417.
8. d) Y. Du, J. Lin, R. Linhardt, J. Carbohydr. Chem. 1997, 16, 1327.
9. H. Yu, B. Yu, X. Wu, Y. Hui, X. Han, J. Chem. Soc., Perkin Trans. 1 2000, 1445.
10. f) T. Zhu, G.-J. Boons, Carbohydr. Res. 2000, 329, 709.
11. g) A. A. Sherman, O. N. Yudina, Y. V. Mironov, E. V. Sukhova, A. S. Shashkov, V. M. Menshov, N. E. Nifantiev, Carbohydr. Res. 2001, 336, 13.
12. h) R. Geurtsen, G.-J. Boons, Tetrahedron Lett. 2002, 43, 9429.
13. i) H. Tanaka, M. Adachi, T. Takahashi, Tetrahedron Lett. 2004, 45, 1433.
14. j) J. Xue, S. D. Khaja, R. D. Locke, K. L. Matta, Synlett 2004, 861.
15. k) J. D. C. Codée, B. Stubba, M. Schiattarella, H. S. Overkleeft, C. A. A. van Boeckel, J. H. van Boom, G. A. van der Marel, J. Am. Chem. Soc. 2005, 127, 3767.
16. a)G.Hirai, T. Watanabe, K. Yamaguchi, T. Miyagi, M. Sodeoka, J. Am. Chem. Soc. 2007, 129, 15420.
17. b) T. Watanabe, G. Hirai, M. Kato, D. Hashizume, T. Miyagi, M. Sodeoka, Org. Lett. 2008, 10, 4167.
18. c) M. Sodeoka, G. Hirai, T. Watanabe, T. Miyagi, Pure Appl. Chem. 2009, 81, 205.
19. Z.Li, J. C. Gildersleeve, J. Am. Chem. Soc. 2006, 128, 11612.
20. Z.Li, J. C. Gildersleeve, Tetrahedron Lett. 2007, 48, 559.
21. T. Mukaiyama, K. Takeuchi, H. Jona, H. Maeshima, T. Saitoh, Helv. Chim. Acta 2000, 83, 1901.
22. a) B. Yu, H. Tao, Tetrahedron Lett. 2001, 42, 2405.
23. b) B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099.
24. W. Peng, X. Han, B. Yu, Synthesis 2004, 1641.
25. Z. Zhang, G. Magnusson, J. Org. Chem. 1996, 61, 2383.
26. M. A. Nashed, M. S. Chowdhary, L. Anderson, Carbohydr. Res. 1982, 102, 99.
27. a) K. W. C. Poon, S. E. House, G. B. Dudley, Synlett 2005, 3142.
28. b) K. W. C. Poon, G. B. Dudley, J. Org. Chem. 2006, 71, 3923.
29. As a recent review: L. K. Mydock, A. V. Demchenko, Org. Biomol. Chem. 2010, 8, 497.
30. Recent example: T. Nokami, Y. Nozaki, Y. Saigusa, A. Shibuya, S. Manabe, Y. Ito, J. Yoshida, Org. Lett. 2011, 13, 1544.
31. Y. Zeng, Z. Wang, D. Whitfield, X. Huang, J. Org. Chem. 2008, 73, 7952.
32. J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090.
33. H. D. Premathilake, L. K. Mydock, A. V. Demchenko, J. Org. Chem. 2010, 75, 1095.
34. L. Chen, F. Kong, Tetrahedron Lett. 2003, 44, 3691.
35. J.-C. Jacquinet, Carbohydr. Res. 2004, 339, 349.
36. Using the same donor as in ref. 17, -selective glycosylation was realized: S. Janssen, R. R. Schmidt, J. Carbohydr. Chem. 2005, 24, 611.
37. Supporting Information is available electronically on the CSJJournal Web site, http://www.csj.jp/journals/chem-lett/index.html.