Disclosed is a process for preparing the glycoside antitumor anthracyclines 7-0-(2,6-dideoxy-.alpha.-L-arabino-hexopyranosyl)-daunomycinone (Ia); 4-demethoxy-7-0-(2,6-dideoxy-.alpha.-L-arabino-hexopyranosyl)-daunomycinon e (Ib); 7-0-(2,6-dideoxy-.alpha.-L-arabino-hexopyranosyl)-adriamycinone (Ic); 4-demethoxy-7-0-(2,6-dideoxy-.alpha.-L-arabino-hexopyranosyl)-adriamycinon e (Id); 7-0-(2,3,6-trideoxy-.alpha.-L-erythro-hex-2-enopyranosyl)-daunomycinone (IIa); 4-demethoxy-7-0-(2,3,6-trideoxy-.alpha.-L-erythro-hex-2-enopyranosyl)-daun omycinone (IIb); 7-0-(2,3,6-trideoxy-.alpha.-L-erythro-hex-2-enopyranosyl)-adriamycinone (IIc); and 4-demethoxy-7-0-(2,3,6-trideoxy-.alpha.-L-erythro-hex-2-enopyranosyl)-adri amycinone (IId). Compounds Ia, Ib, IIa, IIb are prepared by condensing daunomycinone and 4-demethoxydaunomycinone with 3,4-di-0-acetyl-2,6-dideoxy-.alpha.-L-arabino-hexopyranosyl chloride in an inert solvent in the presence of silver triflate (silver trifluoromethansulfonate), as catalyst, and by removing the protecting groups. Analogously the derivatives Ic, Id, IIc and IId are prepared by condensing a novel reactive protected derivative of adriamycinone and 4-demethoxyadriamycinone in the presence of mercuric bromide/mercuric oxide with the above mentioned sugar halide. The new compounds of the invention are useful in treating certain tumors in mammals.

Disclosed is 3'-deamino-3'-morpholino-carminomycin, a new anthracycline glycoside having both antimicrobial and antitumor activity. Also disclosed is a new N-alkylation procedure for preparing the above compound as well as the known anthracyclines, 3'-deamino-3'-morpholino-adriamycin and 3'-deamino-3'-morpholino-daunomycin, in high yield.