Abstract
1,6-Anhydro-β-D-mannopyranose derivatives having electron-withdrawing groups at C-2, i.e., 1,6-anhydro-3,4-di-O-benzyl-2-O-methanesulfonyl-β-D-mannopyranose (5), 1,6-an-hydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-mannopyranose (6), and 1,6-anhydro-3,4-di-O-benzyl-β-D-arabino-hexopyranos-2-ulose (7) were synthesized, and polymerized under cationic conditions. The polymerization of 5 gave stereoregular polysaccharide with high molecular weight. On the other hand, the polymerization of 6 yielded lower molecular weight polysaccharide, and 7 showed no polymerizability under various conditions. Differences in the reactivity among 1,6-anhydro sugar derivatives having various electron-withdrawing groups at C-2 are discussed.
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Kanno, KI., Kobayashi, Y. & Hatanaka, K. Effects of Electron-Withdrawing Groups at C-2 Position of 1,6-Anhydro-Sugars on Their Polymerizabilities. Polym J 27, 71–77 (1995). https://doi.org/10.1295/polymj.27.71
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DOI: https://doi.org/10.1295/polymj.27.71