Synthesis of a phosphatidylinositol dimannoside using 2-(AZIDOMETHYL) benzoate mannosyl donors

Heterocycles

Volumn 89, Issue 3, 2014, Pages 763-774

  Ohira, Shuichi ^a   Yamaguchi, Yoshiki ^b   Takahashi, Takashi ^c   Tanaka, Hiroshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b RIKEN   (Japan)

^c YOKOHAMA COLLEGE OF PHARMACY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896524216     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-14-12944     Document Type: Article

References (37)

1. P. J. Brennan, Tuberculosis, 2003, 83, 91;
2. V. J. Quesniaux, M. D. Nicolle, D. Torres, L. Kremer, Y. Guérardel, J. Nigou, G. Puzo, F. Erard, and B. Ryffel, J. Immunol., 2004, 172, 4425;
3. K. Fischer, E. Scotet, M. Niemeyer, H. Koebernick, J. Zerrahn, S. Maillet, R. Hurwitz, M. Kursar, M. Bonneville, S. H. E. Kaufmann, and U. E. Schaible, Proc. Natl. Acad. Sci. USA, 2004, 101, 10685.
4. J. B. Torrelles, A. K. Azad, and L. S. Schlesinger, J. Immunol., 2006, 177, 1805;
5. G. D. Sprott, C. J. Dicaire, K. Gurnani, S. Sad, and L. Krishnan, Infect. Immun., 2004, 72, 5235;
6. M. Gilleron, J. Nigou, D. Nicolle, V. Quesniaux, and G. Puzo, Chem. Biol., 2006, 13, 39.
7. C. J. J. Elie, R. Verduyn, C. E. Dreef, D. M. Brounts, G. A. Van der Marel, and J. H. Van Boom, Tetrahedron, 1990, 46, 8243;
8. Y. Watanabe, T. Yamamoto, and T. Okazaki, Tetrahedron, 1997, 53, 903;
9. A. Stadelmaier and R. R. Schmidt, Carbohydr. Res., 2003, 338, 2557;
10. K. N. Jayaprakash, J. Lu, and B. Fraser-Reid, Bioorg. Med. Chem. Lett., 2004, 14, 3815;
11. A. Stadelmaier, M. B. Biskup, and R. R. Schmidt, Eur. J. Org. Chem., 2004, 3292;
12. X. Liu, B. L. Stocker, and P. H. Seeberger, J. Am. Chem. Soc., 2006, 128, 3638;
13. G. D. Ainge, H. Davis, G. S. Larsen, G. F. Painter, G. S. Gill, and J. L. Harper, Bioorg. Med. Chem., 2006, 14, 5632;
14. G. D. Ainge, N. A. Parlane, M. Denis, C. M. Hayman, D. S. Larsen, and G. F. Painter, Bioorg. Med. Chem., 2006, 14, 7615;
15. B. Fraser-Reid, S. R. Chaudhuri, K. L. Jayaprakash, J. Lu, and C. V. S. Ramamurty, J. Org. Chem., 2008, 73, 9732;
16. S. Boonyarattanakalin, X. Liu, M. Michieletti, B. Lepenies, and P. H. Seeberger, J. Am. Chem. Soc., 2008, 130, 16791;
17. P. S. Patil and S. C. Hung, Chem. Eur. J., 2009, 15, 1091;
18. A. Ali, M. R. Wenk, and M. J. Lear, Tetrahedron Lett., 2009, 50, 5664;
19. P. S. Patil and S. C. Hung, Org. Lett., 2010, 12, 2618.
20. T. Wada, A. Ohkubo, A. Mochizuki, and M. Sekine, Tetrahedron Lett., 2001, 42, 1061.
21. N. J. Osborn and R. J. Robinson, Tetrahedron, 1993, 49, 2878.
22. K. R. Love, R. B. Andrade, and P. H. Seeberger, J. Org. Chem., 2001, 66, 8165.
23. G. Anilkumar, G. Latha, G. Nair, and B. Fraser-Reid, Org. Lett., 2000, 2, 2587.
24. L. Yang, Q. Qin, and X.-S. Ye, Asian J. Org. Chem., 2013, 2, 30;
25. H. Tanaka, H. Yamada, and T. Takahashi, Trend in Glycosci. Glycotech., 2007, 19, 183;
26. Y. Wang, X.-S. Ye, and L.-H. Zhang, Org. Biomol. Chem., 2007, 5, 2189.
27. H. Yamada, T. Harada, and T. Takahashi, J. Am. Chem. Soc., 1994, 116, 7919;
28. H. Tanaka, M. Adachi, H. Tsukamoto, T. Ikeda, H. Yamada, and T. Takahashi, Org. Lett., 2002, 4, 4213;
29. H. Tanaka, M. Adachi, and T. Takahashi, Tetrahedron Lett., 2004, 45, 1433;
30. M. Adachi, H. Tanaka, and T. Takahashi, Synlett, 2004, 609;
31. H. Tanaka, M. Adachi, and T. Takahashi, Chem. Eur. J., 2005, 11, 849;
32. H. Tanaka, T. Ishida, N. Matoba, H. Tsukamoto, H. Yamada, and T. Takahashi, Angew. Chem. Int. Ed., 2006, 45, 6349;
33. H. Tanaka, Y. Tateno, Y. Nishiura, and T. Takahashi, Org. Lett., 2008, 10, 5597;
34. H. Tanaka, Y. Tanimoto, T. Kawai, and T. Takahashi, Tetrahedron, 2011, 67, 10011.
35. S. L. Bender and R. J. Budhu, J. Am. Chem. Soc., 1991, 113, 9883.
36. B. C. Froehler, P. G. Ng, and M. D. Matteucci, Nucleic Acids Res., 1986, 14, 5399;
37. P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Stronberg, and C. Henrichson, Tetrahedron Lett., 1986, 27, 4051. Technology