Anthracycline glycosides of 2,6-dideoxy-2-fluoro-alpha-L-talopyranose.
The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-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.
Horton
Derek
D
Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, DC 20016, USA. carbchm@american.edu <carbchm@american.edu>
Khare
Anakshi
A
D018943:Anthracyclines / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D045744:Cell Line, Tumor; D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D006801:Humans; D015255:Idarubicin / Q000031:analogs & derivatives* / Q000737:chemistry; D009369:Neoplasms / Q000188:drug therapy
C515779:4-demethoxy-7-O-(2,6-dideoxy-2-fluorotalopyranosyl)adriamycinone; D018943:Anthracyclines; D000970:Antineoplastic Agents; D006027:Glycosides; C075993:4-demethoxydaunomycinone; D004317:Doxorubicin; D015255:Idarubicin