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4-De:methoxy daunorubicin hydrochloride prepn. - from optically active daunomycinone condensed with daunosamine in presence of silver tri:fluoromethyl sulphonate
4-De:methoxy daunorubicin hydrochloride prepn. - from optically active daunomycinone condensed with daunosamine in presence of silver tri:fluoromethyl sulphonate
4-Demethoxy daunorubicin of formula (I) is made from optically-active 4-demethoxy daunomycinone, which is condensed in organic solvent in presence of silver trifluoromethanosulphonate, with a N,O-trifluoroacetyl-protected 1-chloro daunosamine, to obtain the N,O-protected alpha-anomeric glucoside. By elimination of the protective gps., first with methanol and then by mild alkaline hydrolysis, e.g. with dil. aq. NaOH soln., the free glucoside base (I) is obtd., which is isolated as the hydrochloride.
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