METHOD FOR PREPARING ANTIBIOTIC CARMINOMYCINE OR ITS HYDROCHLORIDE Russian patent published in 2005 - IPC

FIELD: organic chemistry, chemical technology, antibiotics.

SUBSTANCE: invention relates to a method for preparing antibiotic carminomycine or its hydrochloride. Method involves glycosylation of carminomycinone with 1,4-di-O-substituted N-acyldaunosamine (2,3,6-trideoxy-3-amino-L-lyxo-hexapyranose) of the formula (3):

wherein R¹ means trifluoroacetyl, N-(9H-fluorene-2-ylmethoxy)carbonyl, allyloxycarbonyl; R² means acetyl, trifluoroacetyl, 4-nitrobenzoyl, allyloxycarbonyl; R³ means trichloroacetamidyl, trialkylsilyl, acetyl, trifluoroacetyl, 4-nitrobenzoyl, allyloxycarbonyl in the presence of trimethylsilyltrifluoromethane sulfonate in mixture of anhydrous aprotonic organic solvents followed by removing blocking groups and isolation of carminomycine as a base or hydrochloride. Glycosyl-donor is used as a mixture of α- and β-isomers or as individual α- or β-isomers. As anhydrous aprotonic organic solvent method involves using mixtures of dioxane with chloroform, methylene chloride, diethyl ether, acetone and tetrahydrofuran. The reaction is carried out in presence of molecular sieves at temperature 10°C, nor above, in atmosphere of dried air or dried inert gas. Removal of protecting groups is carried out in the presence of alkaline metal hydroxides in an aqueous-organic medium: water - methanol, water - dioxane, water - tetrahydrofuran, water - acetone. Method provides increasing yield of carminomycine by 3 times as compared with the prototype.

EFFECT: improved preparing method, enhanced yield.

5 cl, 7 ex