炭水化物系化合物の自動酸化分解(第5報) : Glucoseの自動酸化分解機構について

概要

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N-Aryl-D-glucosylamine was cleaved autoxidatively in ethanol solution containing the same arylamine, and a pigment (1) was isolated from the reaction mixture. When p-toluidine was used, the pigment was obtained as red-brown needles. The result of analysis and the fact that 5-methylisatin was isolated from the hydrolysis of I with hydrochloric acid indicate I to be 2,3-bis-(p-tolylimino)-5-methylisatin (Ia) or 2-(p-tolylamino)-3-(p-tolylimino)-5-methylisatin (Ib). 2,3,4,6-Tetra-o-acetyl-2-oxyglucal (AOGA) and 3,4,6-triacetylglucal (AGA) were cleaved by ammonia, p-toluidine, and cyclohexylamine respectively. When ammonia was used, formic acid and arabonic acid were isolated. In the case of p-toluidine N-(p-tolyl)-2,3,4,6-tetra-o-acetyl-D-glucosylamine (VI) was obtained accompanied with a small amount of oxalic acid, arabonic acid, and azo-p-toluene. When cyclohexylamine was used, oxalic acid and D-arabonic acid were isolated only. The yields of each decomposition products from AOGA was higher than those from AGA. Since acetylated amine was obtained, it was considered that acetyl migration by amine occured first in these reactions, followed by autoxidative decomposition.
公益社団法人日本薬学会の論文
1970-06-25