Epidoxorubicin, Pidorubicin(former Prop INN), 4'-epi-Doxorubicin, 4'-epi-Adriamycin, Epirubicin hydrochloride, 4'-epi-DX, IMI-28, E-ADM, Ellence, Farmorubicina, Pharmorubicin, Farmorubicin-药物合成数据库

【药物名称】Epidoxorubicin, Pidorubicin(former Prop INN), 4'-epi-Doxorubicin, 4'-epi-Adriamycin, Epirubicin hydrochloride, 4'-epi-DX, IMI-28, E-ADM, Ellence, Farmorubicina, Pharmorubicin, Farmorubicin

化学结构式(Chemical Structure):

参考文献No.	199331
标题:	Epirubicin
作者:	Serradell, M.N.; Casta馿r, J.; Hopkins, S.J.; Blancafort, P.
来源:	Drugs Fut 1983,8(5),402

合成路线图解说明: 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.

参考文献No.	607979
标题:	Synthesis and antitumor properties of new glycosides daunomycin and daunorubicin
作者:	Arcamone, F.; Penco, S.; Vigevani, A.; Redaelli, S.; Franchi, G.; Di Marco, A.; Casazza, A.M.; Dasdia, T.; Formelli, F.; Necco, A.; Soranzo, C.
来源:	J Med Chem 1975,18(7),703-707

合成路线图解说明: 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.