Structure-Controlled Synthesis of Regiospecifically Modified Polysaccharides Starting from a Pyrolysis Product of Cellulose

摘要: Starting from a pyrolysis product of cellulose, 1,6-anhydro-β-D-glucopyranose derivatives having regiospecific substituents and protecting groups were prepared. Ring-opening polymerization using these anhydro sugar as monomers, followed by debenzylation, afforded structurally well-defined (1→6)-α-D-glucopyranan (linear dextran) derivatives: (a) 3-O-Methyl-(1→6)-α-D-glucopyranan, (b) 3-O-octadecyl-(1→6)-α-D-glucopyranan, (c) 3-C-methyl-3-O-methyl-(1→6)-α-D-glucopyranan, (d) 3-deoxy-(1→6)-α-D-ribo-hexopyranan, (e) 3,4-dideoxy-(1→6)-α-D-threo-hexopyranan, (f) 2,4-dideoxy-(1→6)-α-D-threo-hexopyranan (g) 2,4-dideoxy-3-O-(β-D-galactopyranosyl)-α-D-threo-hexopyranan. Heteropoly-saccharides with the required amount at relatively uniform intervals also prepared via copolymerization.