Novel lactosamine derivatives
A technology for lactosamine and derivatives, applied in the field of lactosamine derivatives, can solve the problems of low efficiency of synthetic methods, low overall yield, inability to obtain large-scale production methods and the like
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[0060] The preparation of free N-substituted lactosamine bases leads directly to the formation of numerous lactosamine salts in aqueous or anhydrous solutions using the corresponding acids.
[0061] Thus, for example, Heyns rearrangement using N-benzyllactulosylamine can give N-benzyllactosylamine in excellent yields. Subsequent chromatography provides N-benzyl-lactosamine as the pure base. Additional salt formation with acids such as aqueous HCl, anhydrous HCl in MeOH, sulfuric acid, etc. afforded the novel N-substituted lactosamine salts in quantitative yields.
[0062] The present invention provides novel methods of using purified N-substituted lactosamines characterized by general formula 5.
[0063] One of the most important applications of the novel compounds of general formula 5 is the removal of R by hydrogenolysis or any other method known in the art 2 Substituents to generate different lactosamine salts. The reaction can be catalyzed by numerous Pd, Ni or other me...
Embodiment
[0164] General method for preparing optionally substituted malonamides;
[0165] 1 mmol of dimethyl malonate and 2 mmol of alkylamine were mixed in a round bottom flask, and the mixture was stirred until the starting compound was completely reacted. Reaction times vary from 30 minutes to 24 hours, and temperatures range from room temperature to reflux. When the reaction was complete, the product was isolated as a white solid / crystal.
[0166] Yields ranged from 80% to quantitative.
[0167]
[0168] 6 g of dimethyl malonate and 10 g of benzylamine were mixed in a round bottom flask, and the mixture was stirred at 110° C. for 20 minutes. When the reaction was complete, the product was isolated as white crystals (12g).
[0169] 1H NMR. (CDCl 3 )δ: 7.77 (bs, 2H, NH), 7.25 (m, 10H, aromatic), 4.35 and 4.32 (s, 4H, 2×-C H 2 Ph), 3.19(s, 2H, COC H 2 CO).
[0170] 13C NMR (CDCl 3 )δ: 167.69 (2×CO), 137.99, 128.90, 127, 86, 127.86, 127.70 and 127.70 (aromatic), 43.76, 4...
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