Chemistry of glycosylamines. Isopropylidene acetals of N-acetyl-α-d-glucofuranosylamine |
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Authors: | Mariana Galicio Jorge Mosettig María E Gelpi Raúl A Cadenas |
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Institution: | Departamento de Quimica, Facultad de Agronomia, Universidad de Buenos Aires, 1417 Av. San Martin 4453, Buenos Aires Argentina |
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Abstract: | The reaction of N-acetyl-α-d-glucofuranosylamine with 2,2-dimethoxypropane, catalyzed by p-toluenesulfonic acid, gave 1-acetamido-2,3:5,6-di-O-isopropylidene-1-O-methyl-d-glucitol (65.6%), 1-acetamido-2,3-O-isopropylidene-1-O-methyl-d-glucitol (3.7%), and N-acetyl-5,6-O-isopropylidene-α-d-glucofuranosylamine (3.2% yield). The structures of these compounds were determined by chemical and spectroscopic methods, and their relation to the pattern of n.m.r. resonances of the isopropylidene methyl groups is discussed. |
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