Synthesis of Biodegradable Polymer Having Saccharide Chai

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On D-lactose, C-6 and C-6' which have the primary hydroxy groups were selectively triphenylmethylated and the remaining secondary hydroxy groups were acetylated. During detriphenylmethylation, acyl migration occurred to give acetylated lactose having free hydroxy groups on C-6 and C-4'. Polycondensation of the obtained 1,2,3,2',3',6'-hexa-ο-acetyl-D-lactose and terephthaloyl chloride gave the aromatic polyester having lactose in the main chain.Maltose was regioselectively substituted and the obtained derivative was polymerized in order to obtain a biodegradable polymer. Two primary hydroxyl groups of maltose were tosylated and the remaining secondary hydroxyl groups were acetylated. The tosyl group was replaced with azido group. The azidomaltose derivative was reacted with telephthaloyl chloride to give amide compound.Partial carboxymethylation of b-cyclodextrin was investigated. The carboxymethylation of b-cyclodextrin with chloroacetic acid and sodium hydroxide in water sokution was difficult to give the product. On the other hand, di-ο-carboxymethylated b-cyclodextrin was obtained by using potassium hydroxide as base. When bromoacetic acid was used instead of chloroacetic acid, di-ο-carboxymethylated b-cyclodextrin was obtained in shorter time. The reaction of b-cyclodextrin with methyl chloroacetate and sodium hydride in dimethylformamide solusion also gave di-ο-carboxymethylated b-cyclodextrin with the hydrolysis of methyl ester. Condensation reaction of di-ο-carboxymethylated b-cyclodextrin with hexamethylendiamine gave polyamide of which the molecular weight was 10^4.