窒素配糖體の研究 : (第29報)BRIGLs anhydrideを用いる窒素配糖体の合成

概要

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A method for the synthesis of N-glycosides through the condensation of p-toluidine with BRIGLs anhydride (3, 4, 6-triacetyl-D-glucose 1, 2-anhydride) is presented. The reaction mixture of p-toluidine with the anhydride in benzene solution was boiled for 5 minutes or allowed to stand for 24 hours at room temperature to produce a crystal which had the melting point of 133_??_134° and the [α]13D of -44.5° (c 1.6, chloroform). This was proved to be N-p-tolyl-D-glucosylamine 3, 4, 6-triacetate, and by acetylation to yield N-p-tolyl-β-D-glucosylamine 2, 3, 4, 6-tetraacetate, which was shown to be identical with the specimen prepared by the acetyl-ation of N-p-tolyl-β-D-glucosylamine. On the other hand it was found that condensation by melting both reactants without solvent gave the same reaction product as that of the condensation in benzene. Concerning the result of the present experiment, the mechanism of the AMADORI rearrangement was discussed, and the possibility for the rearrangement of the reaction product obtained when BRIGLs anhydride was melted with p-toluidine was also discussed and taken into consideration. The reaction condition of melting might be expected. to have the possibility of the AMADORI rearrangement, but it was found that no intramolecular rearrangement occurred. The advantage of applying this method for further synthesis of N-glycosides is mentioned.
社団法人日本農芸化学会の論文