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【结 构 式】

【分子编号】34075

【品名】2-[(8S,10R,11R,14S,17R)-11,17-dihydroxy-10-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate

【CA登记号】

【 分 子 式 】C22H30O6

【 分 子 量 】390.4766

【元素组成】C 67.67% H 7.74% O 24.58%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

The starting product being 21-acetoxy-11alpha,17alpha-dihydroxy-pregn-4-ene-3,20-dione (I). The first step is the ketalization of (I) giving the ethylenedioxy derivative (II), which is epoxidized with monoperphthalic acid (B) to the epoxide (III), then the epoxide ring is opened with HF giving the fluoro derivative (IV); its bromination in dioxane affords (V), which by reaction with methanesulfonyl chloride gives the mesyl ester (VI). This compound is acetylated with acetic anhydride to the triacetoxy derivative (VII), which by treatment first with sodium acetate and then with bromine gives the mono unsaturated dibromo compound (VIII). This product by treatment with lithium carbonate and lithium bromide is converted into the triene derivative (IX); this product by treatment with 1,3-dibromo-5,5-dimethylhydantoine (C) adds BrOH giving (X), which is epoxidized by treatment with potassium carbonate yielding (Xl). This epoxide ring is finally opened with HF.

1 Riva, M.; Toscano, L.; 2-Bromo-6beta-fluoropregna-1,4-3,20-diones. BE 0826030; DE 2533377; ES 455934; FR 2261776; GB 1499822 .
2 Castaner, J.; de Angelis, L.; Halopredone diacetate. Drugs Fut 1976, 1, 11, 526.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(B) 34077 2-carboperoxybenzoic acid C8H6O5 详情 详情
(I) 34075 2-[(8S,10R,11R,14S,17R)-11,17-dihydroxy-10-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate C22H30O6 详情 详情
(II) 34076   C25H36O7 详情 详情
(III) 34078 (5α,6α,11α)-21-(acetyloxy)-5,6-epoxy-11,17-dihydroxypregnane-3,20-dione cyclic 3-(1,2-ethanediyl acetal) 57781-08-5 C25H36O8 详情 详情
(IV) 34079 2-[(5R,6R,8S,10R,11R,13S,14S,17R)-6-fluoro-5,11,17-trihydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate 913-49-5 C23H33FO7 详情 详情
(V) 34080 2-[(2R,5R,6R,8S,10R,11R,13S,14S,17R)-2-bromo-6-fluoro-5,11,17-trihydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate 57781-10-9 C23H32BrFO7 详情 详情
(VI) 34081 2-((2R,5R,6R,8S,10R,11R,13S,14S,17R)-2-bromo-6-fluoro-5,17-dihydroxy-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate C26H38BrFO7S 详情 详情
(VII) 34082 (2R,5R,6R,8S,10R,11R,13S,14S,17R)-5-(acetoxy)-17-[2-(acetoxy)acetyl]-2-bromo-6-fluoro-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate C30H42BrFO9S 详情 详情
(VIII) 34083 (6R,8S,10R,11R,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2,2-dibromo-6-fluoro-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate C28H37Br2FO7S 详情 详情
(IX) 34084 (6R,8S,10R,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2-bromo-6-fluoro-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl acetate 57808-78-3 C25H28BrFO6 详情 详情
(X) 34085 (6R,8S,9R,10S,11S,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2,9-dibromo-6-fluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl acetate 57781-13-2 C25H29Br2FO7 详情 详情
(XI) 34086 (4aS,4bS,5aS,6aS,7R,9aS,9bS,11R)-7-[2-(acetoxy)acetyl]-3-bromo-11-fluoro-4a,6a-dimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-7-yl acetate C25H28BrFO7 详情 详情
(C) 31277 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione 77-48-5 C5H6Br2N2O2 详情 详情
Extended Information