N, n-dimethyl-d-glucosamine tetraacetyl

The invention comprises 1,3,4,6-tetraacetyl-N,N-dimethyl-D-glucosamine and its salts prepared by treating 1,3,4,6-tetraacetyl-D-glucosamine with formaldehyde and hydrogen in the presence of a hydrogenation catalyst and in an inert solvent at room temperature, and isolating the product preferably as...

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Hauptverfasser: BADER ROLF RENE, MOREL CHARLES JOSEPH
Format: Patent
Sprache:eng
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Zusammenfassung:The invention comprises 1,3,4,6-tetraacetyl-N,N-dimethyl-D-glucosamine and its salts prepared by treating 1,3,4,6-tetraacetyl-D-glucosamine with formaldehyde and hydrogen in the presence of a hydrogenation catalyst and in an inert solvent at room temperature, and isolating the product preferably as its salt. Raney nickel, and platinum oxide or palladium on carriers such as charcoal, barium sulphate or carbonate can be used as catalysts and hydrochloric, hydrobromic, sulphuric, oxalic or maleic acids are added to form salts which are separated, and the base liberated therefrom if desired. N,N-dimethyl-D-glucosamine may be formed by further hydrolysis with aqueous mineral acid e.g. 0.5-3N hydrochloric acid. The compound may be reacted with acetylbromide to form a -bromo - 3,4,6 - triacetyl-N,N-dimethylglucosamine hydrobromide, which may be reacted with the sodium salt of o -benzylphenol or 2,6-dimethyl phenol to form 3,4,6-triacetyl - b - (o - benzylphenyl)-N,N-dimethyl-D-pyranoglucosaminide, which with ammonia in aqueous methanol forms b -(o -benzylphenyl) - N,N-dimethyl-D-pyranoglucosaminide or which may be reacted with methyl halides to form methohalides, or 3,4,6-triacetyl-b -(2161-dimethylphenyl)-N, N-dimethyl-D-pyranolglucosaminide which may be quaternised with methyl halides.