PROCESS FOR THE PREPARATION OF ANOMER PURE GLYCOSIDES OF AROMATIC AMINES

摘要

The present invention is directed to a new process for preparing anomer pure N-glycosides or acid additon salts thereof of general formula (I), wherein R stands for a glycosyl group, n stands for 1, 2 or 3, A stands for an aromatic system, selected from a benzene ring, a 5-membered ring containing 1 heteroatom, the heteroatom being nitrogen and a 6-membered ring containing 2 heteroatoms, the heteroatoms being nitrogen or nitrogen and sulfur, a 6-membered ring containing 3 heteroatoms, the heteroatoms being nitrogen, a condensed ring system consisting of 2 or 3 rings, one member of which is the above ring, with the provision that the glycoside nitrogen atom(s) is (are) attached to aromatic nucleus (nuclea), S stands for an acid residue, p stands for 1, 2 or 3, m stands for 0 or 1, R1 and R2 are the same or different, and stand for hydrogen, halogen, amino-, sulfonamido-, nitro-, C1-4 straight or branched saturated or unsaturated alkyl or alkoxy group, carboxyl, C1-4 carbalkoxy, phenyl, substituted phenyl, heterocyclic or substituted heterocyclic group, by reacting a compound of general formula (II) or an acid addition salt thereof, wherein R1, R2, A, X, n, p and m are as given above, with the provision that the amino group(s) to be glycosylated is (are) attached to aromatic nucleus (nuclea) - with hexose, pentose, desoxy-, desoxy-amino, hexose or pentose derivatives or oligosaccharides in the presence of a protic acid catalyst which comprises carrying out the reaction in water preferably in the presence of hydrochloric acid in a catalytic amount at a temperature of 18-90°C and isolating the product preferably by a direct filtration of the reaction mixture, or by separating first with an organic solvent, preferably ethanol, acetone or a mixture of ethanol and acetone and drying the product subsequently.