Penta-O-acetyl-tetra-N-ethoxycarbonyl-6''-O-tritylkanamycin* was prepared, and, after detritylation, oxidized with potassium permanganate in acetic acid. The oxidation product was esterified with diazomethane to give methyl penta-O-acetylH:etra-N-ethoxycarbonylkanamycin-6''-uronate. Hydrolysis of the product with barium hydroxide followed by column chromatography and esterification with methanolic hydrogen chloride afforded methyl kanamycin-6"-uronate. Hydrolysis of the ester with dilute hydrochloric acid afforded kanamycin-6''-uronic acid. The ester was converted into its amide. An alternative oxidation of tetra-N-benzyloxycarbonylkanamycin using platinum and oxygen also led to the same uronic acid. The antibiotic spectra of the uronic acid and its ester and amide are described.
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Kobayashi et al. (1970) studied this question.
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