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

表阿霉素Chemical Name: (1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside hydrochloride; (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-arabinohexopyranosyl)oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride
CAS No. 56420-45-2 (free base)
项目整合开发状态: Launched-1984
项目研究机构: Pfizer (Originator), Kyowa Hakko (Not Determined), National Cancer Institute (Not Determined)
合成路线: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.