SYNTHESIS AND ANTITUMOR-ACTIVITY OF ANTHRACYCLINE DISACCHARIDE GLYCOSIDES CONTAINING DAUNOSAMINE

Daunosamine, as its 4-O-acetyl-3-N-trifluoroacetyl glycosyl chloride d erivative (1b), has been coupled alpha-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives Of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycoside s by sequential alkoxyiodination-tributylstannane reduction has been e valuated. The sequence successfully demonstrated with the methyl glyco sides was successfully extended with daunomycinone as the aglycon, pro viding a preparative route to ideoxy-alpha-L-arabino-hexopyranosyl]dau nomycinone hydrochloride (15), an analogue of natural anthracycline an tibiotics containing daunosamine and a 2,6-dideoxy-L-hexose.