Synthesis of D-xylopyranan by the ring-opening polymerization of 3-O-benzyl-alpha-D-xylopyranose 1,2,4-orthopivalate. Attempts to synthesize a stereoregular polymer.
3-O-Benzyl-alpha-D-xylopyranose 1,2,4-orthopivalate (1) was newly synthesized and polymerized under cationic polymerization reaction conditions in order to synthesize stereoregular (1-->4)-beta-D-xylopyranan. Although the polymerization of orthopivalate 1 was carried out under various reaction conditions, a non-stereoregular polymer, but mainly consisting of (1-->4)-beta-xylopyranose units, was obtained. Comparing these results with those of glucose 1,2,4-orthopivalates, it was revealed that not only the substituents in the C-2 and C-3 positions, but also the CH(2)OR group in glucose 1,2,4-orthopivalate, largely contribute to (1-->4)-beta-glucosidic bond formation by the ring-opening polymerization.
Hori
M
M
Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, 606-8502, Kyoto, Japan.
Nakatsubo
F
F
D002236:Carbohydrate Conformation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014631:Valerates / Q000138:chemical synthesis* / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
C435777:3-O-benzyl-xylopyranose-1,2,4-orthopivalate; D007202:Indicators and Reagents; D011134:Polysaccharides; D014631:Valerates; C431715:xylopyranose; D014994:Xylose