合成路线1

A suspension of methyl 2,3,6-trideoxy-3-amino-alpha-L-lyxo-hexopyranoside (I) is acylated with trifluoroacetic anhydride in ether yielding methyl 2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-lyxo-hexopyranoside (II), which is oxidized with potassium periodate and ruthenium dioxide in CH2Cl2 water to afford methyl 2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-threo-hexapyranosid-4-ulose (III). The reduction of (III) with NaBH4 in dioxane-water gives methyl 2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranoside (IV), which is demethylated by treatment with aqueous acetic acid to yield 2,3,6-trideoxy-4-trifluoroacetamido-alpha-L-arabino-hexopyranose (V). Acylation of (V) with trifluoroacetic anhydride in ether affords 2,3,6-trideoxy-3-trifluoroacetamido-1,4-di-O-trifluoroacetyl-alpha-L-arabino-hexopyranose (VI), which by treatment with dry HCl in ether is converted into 2,3,6-trideoxy-3-trifluoroacetamido-4-O-trifluoroacetyl-alpha-L-arabino-hexopyranosyl chloride (VII). The condensation of (VII) with 9-deacetyl-9-(2',2'-dimethyl-4'-methoxydioxolan-4'-yl)daunomycinone (VIII) [prepared from adriamycinone (IX) and 2,2-dimethoxypropane-p-toluenesulfonic acid in dioxane - CHCl3] by means of HgO and HgBr2 in CH2Cl2 gives 4'-epi-3'-N-trifluoroacetyladriamycin protected in the hydroxylacetyl group (X). Finally, this compound is deprotected by treatment with NaOH in acetone water.