窒素配糖體の研究 : (第30報) p-Toluidine-N-D-fructosideについて

概要

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Recently BARRY and HONEYMAN (1952) have prepared N-p-tolyl-D-fructosyl amine whose physical constants have heen described to be m. p. 138° (decomp.) and [α] D - 208° → -188° (EtOH); - 200° → -167° (pyridine), which differ from our previous description (1948) m. p.154° (decomp.) and [α] D -168° → - 88° (MeOH). Their preparation is made by refluxing p-toluidine and D-fructose with p-toluidine hydrochloride as a catalyst in anhydrous EtOH for 7 minutes while ours with acetic acid as a catalyst for 1 hour. Both methods have been carefully traced and two prepartions, having m.p. 154°, [α]D-220°→ -175° and m.p. 154°, [α] D -219°→ -170° (both in EtOH), respectively, have been obtained, which offer evidence of their identity. This has been confirmed further by preparing their tetracetes in pyridine and acetic anhydride, which show m.p. 130° [α]D-141° and m.p, 130.5°, [α]D-140° (both in CHCl3), respectively. Possibilities of isomerization during the prepar tion process depending upon the subtle differences of reaction condition have been considered, which might cause minor differences in physical constants in two N-D-fructosyl amines prepared at different places, and it has been sug gested that the difference of the data in both the original papers may not be due to these factors.
社団法人日本農芸化学会の論文