D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module

Organic Letters

Volumn 10, Issue 13, 2008, Pages 2685-2688

  Abe, Hajime ^a,b   Horii, Asuka ^a   Matsumoto, Shinya ^c   Shiro, Motoo ^d   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^d RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CARBOHYDRATES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 51649095672     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800783a     Document Type: Article

References (55)

1. Reviews for saccharide recognition by synthetic host: (a) Penadés, S., Ed. Host-Guest Chemistry-Mimetic Approaches to Study Carbohydrate Recognition; Top. Curr. Chem. Vol. 218; Springer-Verlag: Berlin, Germany, 2002.
2. (b) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978-2996.
3. 3v-symmetrical host molecules: (a) Mazik, M.; Buthe, A. C. J. Org. Chem. 2007, 72, 8319-8326.
4. (b) Mazik, M.; Cavga, H.; Jones, P. G. J. Am. Chem. Soc. 2005, 127, 9045-9052.
5. (c) Mazik, M.; Radunz, W.; Boese, R. J. Org. Chem. 2004, 69, 7448-7462.
6. (d) Mazik, M.; Sicking, W. Chem.-Eur. J. 2001, 7, 664-670.
7. (e) Nativi, C.; Cacciarini, M.; Francesconi, O.; Moneti, G.; Roelens, S. Org. Lett. 2007, 9, 4685-4688.
8. (f) Nativi, C.; Cacciarini, M.; Francesconi, O.; Vacca, A.; Moneti, G.; Ienco, A.; Roelens, S. J. Am. Chem. Soc. 2007, 129, 4377-4385.
9. (g) Cacciarini, M.; Cordiano, E.; Nativi, C.; Roelens, S. J. Org. Chem. 2007, 72, 3933-3936.
10. (h) He, C.; Lin, Z.; He, Z.; Duan, C.; Xu, C.; Wang, Z.; Yan, C. Angew. Chem., Int. Ed. 2008, 47, 877-881.
11. Recent examples of saccharide recognition by phenolic host: (a) Mazik, M.; König, A. Eur. J. Org. Chem. 2007, 3271-3276.
12. (b) Goto, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2007, 129, 9168-9174.
13. (c) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
14. (d) Bähr, A.; Droz, A. S.; Püntener, M.; Neidlein, U.; Anderson, A.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1998, 81, 1931-1963.
15. (e) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1600.
16. (f) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306.
17. (g) Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. Am. Chem. Soc. 1989, 111, 5397-5404. See also ref 2g.
18. Recent examples of saccharide recognition by other kinds of hydrogen-bonding host molecules: (a) Klein, E.; Ferrand, Y.; Barwell, N. P.; Davis, A. P. Angew. Chem., Int. Ed. 2008, 47, 2693-2696.
19. (b) Ferrand, Y.; Crump, M. P.; Davis, A. P. Science 2007, 318, 619-622.
20. (c) Klein, E.; Ferrand, Y.; Auty, E. K.; Davis, A. P. Chem. Commun. 2007, 2390-2392.
21. (d) Klein, E.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2005, 44, 298-302.
22. (e) Velasco, T.; Lecollinet, G.; Ryan, T.; Davis, A. P. Org. Biomol. Chem. 2004, 2, 645-647.
23. (f) Lecollinet, G.; Dominey, A. P.; Velasco, T.; Davis, A. P. Angew. Chem., Int. Ed. 2002, 41, 4093-4096.
24. (g) Ryan, T. J.; Lecollinet, G.; Velasco, T.; Davis, A. P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4863-4866.
25. (h) Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1998, 37, 2270-2273.
26. (i) Mazik, M.; Buthe, A. C. Org. Biomol. Chem. 2008, 6, 1558-1568.
27. (j) Mazik, M.; Cavga, H. J. Org. Chem. 2006, 71, 2957-2963.
28. (k) Mazik, M.; Kuschel, M.; Sicking, W. Org. Lett. 2006, 8, 855-858.
29. (l) Li, C.; Wang, G.-T.; Yi, H.-P.; Jiang, X.-K.; Li, Z.-T.; Wang, R.-X. Org. Lett. 2007, 9, 1797-1800.
30. (m) Hou, J.-L.; Shao, X.-B.; Chen, G.-J.; Zhou, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2004, 126, 12386-12394.
31. (n) Lu, W.; Zhang, L.-H.; Ye, X.-S.; Su, J.; Yu, Z. Tetrahedron 2006, 62, 1806-1816.
32. (o) Fang, J.-M.; Selvi, S.; Liao, J.-H.; Slanina, Z.; Chen, C.-T.; Chou, P.-T. J. Am. Chem. Soc. 2004, 126, 3559-3566.
33. (p) Ishi-i, T.; Mateos-Timoneda, M. A.; Timmerman, P.; Crego-Calama, M.; Reinhoudt, D. N.; Shinkai, S. Angew. Chem., Int. Ed. 2003, 42, 2300-2305.
34. (q) Segura, M.; Bricoli, B.; Casnati, A.; Muñoz, E. M.; Sansone, F.; Ungaro, R.; Vicent, C. J. Org. Chem. 2003, 68, 6296-6303.
35. (r) Kim, Y.-H.; Hong, J.-I. Angew. Chem., Int. Ed. 2002, 41, 2947-2950.
36. (s) Ladomenou, K.; Bonar-Law, R. P. Chem. Commun. 2002, 2108-2109.
37. Abe, H.; Aoyagi, Y.; Inouye, M. Org. Lett. 2005, 7, 59-61.
38. (a) Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059-3061.
39. (b) Waki, M.; Abe, H.; Inouye, M. Chem.-Eur. J. 2006, 12, 7639-7647.
40. (c) Abe, H.; Masuda, N.; Waki, M.; Inouye, M. J. Am. Chem. Soc. 2005, 127, 16189-16196.
41. (d) Inouye, M.; Waki, M.; Abe, H. J. Am. Chem. Soc. 2004, 126, 2022-2027.
42. A D3h-symmetrical capsular host molecule has been studied for saccharide recognition: Francesconi, O.; Ienco, A.; Moneti, G.; Nativi, C.; Roelens, S. Angew. Chem., Int. Ed. 2006, 45, 6693-6696.
43. Uchida, K.; Watanabe, H.; Kitahara, T. Tetrahedron 1998, 54, 8975-8984.
44. Sakai, T.; Miyata, K.; Utaka, M.; Takeda, A. Tetrahedron Lett. 1987, 28, 3817-3818. We modified the procedure to reduce the side product, benzylic iodide, by treatment with zinc powder. Attempts of hydrogenolysis conditions ended in failure.
45. Rodríguez, J. G.; Esquivias, J.; Lafuente, A.; Díaz, C. J. Org. Chem. 2003, 68, 8120-8128.
46. See also : Rodríguez, J. G.; Tejedor, J. L. J. Org. Chem. 2002, 67, 7631-7640.
47. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173-6177.
48. Zhou, Q. J.; Worm, K.; Dolle, R. E. J. Org. Chem. 2004, 69, 5147-5149.
49. Boullanger, P.; Chevalier, Y.; Croizier, M.-C.; Lafont, D.; Sancho, M.-R. Carbohydr. Res. 1995, 278, 91-101.
50. 2, 1:2 association could not be excluded at the higher concentration, the curve-fitting analysis produced no meaningful information.
51. For recent reviews of organogels, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3160.
52. (b) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247.
53. (c) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266.
54. (d) Shinkai, S.; Murata, K. J. Mater. Chem. 1998, 8, 485-495.
55. (e) Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201-1217.