Abstract
We report herein studies of ring-opening polymerization of 1,4-anhydro-2,3-di-O-t-butyldimethylsilyl-α-L-arabinopyranose (ADSA) and 1,4-anhydro-2,3-di-O-p-bromobenzyl-α-L-arabinopyranose (ADBA) by cationic initiation in methylene chloride. Polymerization of ADSA using phosphorus pentafluoride as initiator at −60°C gave stereoregular (1→5)-α-L-arabinofuranan derivatives in 85% yield. Polymerization of ADBA with various Lewis acids afforded slightly less stereoregular polymers (α-content 90%) under optimum conditions. Deprotection of both substituted polymers resulted in a free polysaccharide having the same structure, (1→5)-α-L-arabinofuranan. The polymer structure was characterized by 13C NMR spectroscopy, specific rotation, and the methylation analysis using GC-MS spectroscopy.
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References
T. Uryu, K. Kitano, K. Ito, J. Yamanouchi, and K. Matsuzaki, Macromolecules, 14, 1 (1981).
T. Uryu, J. Yamanouchi, T. Kato, S. Higuchi, and K. Matsuzaki, J. Am. Chem. Soc., 105, 6865 (1983).
T. Uryu, J. Yamanouchi, S. Hayashi, H. Tamaki, and K. Matsuzaki, Macromolecules, 16, 320 (1983).
A. Hagino, S. Yoshida, T. Shinpuku, K. Matsuzaki, and T. Uryu, Macromolecules, 19, 1 (1986).
J. Kops and C. Schuerch, J. Polym. Sci., C, 11, 119 (1965).
Y. Koyama, K. Harima, K. Matsuzaki, and T. Uryu, J. Polym. Sci., Polym. Chem. Ed., 23, 2989 (1985).
P. Köll, S. Deyhim, and K. Heyns, Chem. Ber., 106, 3565 (1973).
G. H. Hakimelahi, Z. A. Proba, and K. K. Ogilvie, Tetrahedron Lett., 22, 4775 (1981).
T. Uryu, H. Tachikawa, K. Ohaku, K. Terui, and K. Matsuzaki, Makromol. Chem., 178, 1929 (1977).
F. J. Good, Jr. and C. Schuerch, Macromolecules, 18, 595 (1985).
L. V. Backinouisky, S. A. Nepogodév, and N. K. Kochetkov, Carbohydr. Res., 137, C1 (1985) and references cited therein.
S. Hakomori, J. Biochem., 55, 205 (1964).
H. H. Björndal, C. G. Hellerqvist, B. Lindberg, and S. Svensson, Angew. Chem. Int. Ed., 9, 610 (1970).
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Yoshida, T., Kida, M. & Uryu, T. Selective Ring-Opening Polymerization of Di-O-t-butyldimethylsilylated and Di-O-p-bromobenzylated 1,4-Anhydro-α-L-arabinopyranoses and Structural Analysis of Free Arabinans. Polym J 19, 923–931 (1987). https://doi.org/10.1295/polymj.19.923
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DOI: https://doi.org/10.1295/polymj.19.923
