Synthesis of a regiospecifically fluorinated polysaccharide 3-deoxy-3-fluoro-(1→6)-α-D-glucopyranan via ring-opening polymerization

Macromolecules

Volumn 30, Issue 21, 1997, Pages 6531-6535

  Kobayashi, Kazukiyo ^a   Kondo, Tatsuru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COPOLYMERIZATION; FLUORINE CONTAINING POLYMERS; HALOGENATION; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

DEOXYFLUORINATION; DEOXYFLUOROGLUCOPYRANAN; FLUORINATED POLYSACCHARIDES;

POLYSACCHARIDES;

EID: 0031244953     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma970691s     Document Type: Article

References (27)

1. Penglis, A. A. E. In Advances in Carbohydrate Chemistry and Biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1981; Vol. 38, pp 195-285.
2. Fluorinated Carbohydrates. Chemical and Biological Aspects; Taylor, N. F., Ed.; American Chemical Society: Washington DC, 1987; Vol. 374.
3. Tsuchiya, T. In Advances in Carbohydrate Chemistry and Biochemistry Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1990; Vol. 48, pp 91-277.
4. Glaudemans, C. P. J. Chem. Rev. 1991, 91, 25-33.
5. Ojima, I.; McCarthy, J. R.; Welch, J. T. In Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series, No. 639; American Chemical Society: Washington, DC, 1996.
6. Wall, L. A. Fluoropolymers; Wiley Interscience: New York, 1972.
7. Furukawa, T. Phase Transitions 1989, 18, 143.
8. Kasuya, K.; Iiyama, K.; Ishizu, A. Carbohydr. Res. 1992, 229, 131-139.
9. Goto, K.; Muramoto, M.; Yoshioka, M.; Shiraishi, N. Mokuzai Gakkaishi 1991, 37, 57.
10. Withers, S. G. Carbohydr. Res. 1990, 197, 61-73.
11. Schuerch, C. In Advances in Carbohydrate Chemistry and Biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1981; Vol. 39, pp 157-212.
12. Kochetkov, N. K. Tetrahedron 1987, 43, 2389-2436.
13. Kobayashi, K. In Biotechnology and Polymers; Gebelein, C. G., Ed.; Plenum: Boston, 1991; pp 167-180.
14. Uryu, T. Prog. Polym. Sci. 1993, 18, 717-761.
15. Kobayashi, K. Macromol. Symp. 1995, 99, 157-167.
16. Faghih, R.; Escribano, C. F.; Castillon, S.; Garcia, J.; Lucas, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1986, 51, 4558-4564
17. Sarda, P.; Escribano, F. C.; Alves, R. J.; Olesker, A.; Lukacs, G. J. Carbohydr, Chem. 1989, 8, 115-123.
18. Phillips, L.; Wray, V. J. Chem. Soc. B 1971, 1618-1624.
19. Wray, V. J. Chem. Soc., Perkin Trans. 2 1976, 1598-1605.
20. Csuk, R.; Glanzer, B. I. In Advances in Carbohydrate Chemistry and Biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1988; Vol. 46, pp 73-332.
21. Kovac, P.; Yeh, J. C.; Glaudemans, C. P. J. Carbohydr. Res. 1987, 169, 23-34.
22. Hudlicky, M. In Organic Reactions; John Wiley & Sons, Inc.: New York, 1988; Vol. 35, pp 513-637.
23. Armarego, W. L. F.; Milloy, B. A.; Pendergast, W. J. Chem. Soc., Perkin Trans, 1 1976, 2229-2237.
24. The neighboring group participation was suggested by Prof. Hiroshi Ohrui of Tohoku Univeristy, whom the authors wish to thank.
25. Kobayashi, K.; Sumitomo, H.; Shiozawa, H. Polym. J. 1989, 21, 137-146.
26. Shafizadeh, F.; Furneaux, R.; Cochran, T. G.; Scholl, J. P.; Sakai, Y. J. Appl. Polym. Sci. 1979, 23, 3525-3539.
27. Iversen, T.; Bundle, D. R. Can. J. Chem. 1982, 60, 299-303.