Diastereomixture and racemate of myo-inositol derivatives, stronger organogelators than the corresponding homochiral isomers

Organic Letters

Volumn 6, Issue 10, 2004, Pages 1547-1550

  Watanabe, Yutaka ^a   Miyasou, Tomomi ^a   Hayashi, Minoru ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INOSITOL; MANDELIC ACID DERIVATIVE; O ACETYLMANDELIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; DIASTEREOISOMER; RACEMIC MIXTURE;

GELS; INOSITOL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 2542641042     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049737+     Document Type: Article

References (32)

1. (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3160.
2. (b) Esch, J. H. v.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266.
3. (c) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247.
4. Our latest paper concerning PIPs synthesis: Han, F.; Hayashi, M.; Watanabe, Y. Chem. Lett. 2003, 32, 724-725.
5. As an inositol-based gelator, 4 was very recently reported. Hosoda, A.; Nomura, E.; Miyake, Y.; Taniguchi, H. Chem. Lett. 2003, 32, 1042-1043.
6. Our group and Hosoda et al. independently reported the same phenomena concerning diastereomeric organogelators: (a) Watanabe, Y.; Miyasou, T.; Hamasaki, Y.; Hayashi, M. 83rd National Meeting of the Chemical Society of Japan, March, 2003, Tokyo; Abstract No. 1, p 381. (b) Hosoda, A.; Nomura, E.; Taniguchi, H. 83rd National Meeting of the Chemical Society of Japan, March, 2003, Tokyo; Abstract No. 1, p 505.
7. Our group and Hosoda et al. independently reported the same phenomena concerning diastereomeric organogelators: (a) Watanabe, Y.; Miyasou, T.; Hamasaki, Y.; Hayashi, M. 83rd National Meeting of the Chemical Society of Japan, March, 2003, Tokyo; Abstract No. 1, p 381. (b) Hosoda, A.; Nomura, E.; Taniguchi, H. 83rd National Meeting of the Chemical Society of Japan, March, 2003, Tokyo; Abstract No. 1, p 505.
8. (a) Mukkamala, R.; Weiss, R. G. J. Chem. Soc., Chem. Commun. 1995, 375-376.
9. (b) Vassilev, V. P.; Wood, M. R.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1998, 1865-1866.
10. Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4328-4334.
11. (a) Luo, X.; Liu, B.; Liang, Y. Chem. Commun. 2001, 1556-1557.
12. (b) Hanabusa, K.; Kobayashi, H.; Suzuki, M.; Kimura, M.; Shirai, H. Colloid Polym. Sci. 1998, 276, 252-259.
13. (c) Hanabusa, K.; Maesaka, Y.; Kimura, M.; Shirai, H. Tetrahedron Lett. 1999, 40, 2385-2388.
14. (d) Maitra, U.; Potluri, V. K.; Sangeetha, N. M.; Babu, P.; Raju, A. R. Tetrahedron: Asymmetry 2001, 12, 477-480.
15. (a) Kimura, T.; Yamashita, T.; Koumoto, K.; Shinkai, S. Tetrahedron Lett. 1999, 40, 6631-6634.
16. (b) Ihara, H.; Sakurai, T.; Yamada, T.; Hashimoto, T.; Takafuji, M.; Sagawa, T.; Hachisako, H. Langmuir 2002, 18, 7120-7123.
17. (c) Takafuji, M.; Sakurai, T.; Yamada, T.; Hashimoto, T.; Kido, N.; Sagawa, T.; Hachisako, H.; Ihara, H. Chem. Lett. 2002, 548-549.
18. D'Aléo, A.; Pozzo, J.-L.; Pages, F.; Schmutz, M.; Mieden-Gundert, G.; Vögtle, F.; Caplar, V.; Zinic, M. Chem. Commun. 2004, 190-191.
19. (a) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1993, 1382-1384.
20. (b) Maitra, U.; Kumar, P. V.; Chandra, N.; D'Souza, L. J.; Prasanna, M. D.; Raju, A. R. Chem. Commun. 1999, 595-5596.
21. (c) Jung, J. H.; Ono, Y.; Hanabusa, K.; Shinkai, S. J. Am. Chem. Soc. 2000, 122, 5008-5009.
22. (d) Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319-320.
23. (e) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616.
24. (f) Willemen, H. M.; Vermonden, T.; Marcelis, A. T. M.; Sudhölter, E. J. R. Langmuir 2002, 18, 7102-7106.
25. (g) Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754-10758.
26. (h) Kawano, S.; Fujita, N.; Shinkai, S. Chem. Commun. 2003, 1352-1353.
27. Snip, E.; Koumoto, K.; Shinkai, S. Tetrahedron 2002, 58, 8863-8874.
28. Luboradzki, R.; Gronwald, O.; Ikeda, A.; Shinkai, S. Chem. Lett. 2000, 1148-1149.
29. Han, F.; Hayashi, M.; Watanabe, Y. Tetrahedron 2003, 59, 7703-7711.
30. (a) Luboradzki, R.; Gronwald, O.; Ikeda, M.; Shinkaia, S.; Reinhoudt, D. N. Tetrahedron 2000, 56, 9595-9599.
31. (b) Gronwald, O.; Sakurai, K.; Luboradzki, R.; Kimura, T.; Shinkai, S. Carbohydr. Res. 2001, 331, 307-318.
32. (c) Tamaru, S.; Luboradzki, R.; Shinkai, S. Chem. Lett. 2001, 336-337.