Anthracycline glycosides of 2,6-dideoxy-2-fluoro-alpha-L-talopyranose

摘要

The methyl P-glycoside of the title sugar,obtained from 2-deoxy-2-fluoro-(3-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates,was converted by acetolysis-bromination into 3,4-di-0-acetyl-2,6-dideoxy-2-flu-oro-alpha-L-talopyranosyl bromide,coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)daunomycinone (19).The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue,the antitumor-active 4-demethoxyadriamycinone glycoside 21.