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【结 构 式】

【分子编号】27467

【品名】(3S,5R,8R,9S,10S,13R,17R)-3-(2-aminoethoxy)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol

【CA登记号】

【 分 子 式 】C25H39NO3

【 分 子 量 】401.5896

【元素组成】C 74.77% H 9.79% N 3.49% O 11.95%

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:(VIII)

Reaction of furylandrostanediol (I) (J Chem Soc (C) 1966, 377) with bromoacetaldehyde diethylacetal (II) in the presence of NaH in refluxing tetahydrofuran provided ether (III). Subsequent acid hydrolysis of ethyl acetal of (III) gave aldehyde (IV), which was reduced to alcohol (V) with NaBH4. Coupling of (V) with phthalimide (VI) under Mitsunobu conditions produced the N-alkylated phthalimide (VII), and further hydrazinolysis yielded primary amine (VIII). The required guanidine function was finally introduced by treatment of (VIII) with 3,5-dimethyl-1-pyrazolylformamidinium nitrate (IX) in boiling EtOH.

1 Quadri, L.; Bernardi, L.; Ferrari, P.; Gobbini, M.; Melloni, P.; Valentino, L. (Sigma-Tau Industrie Farmaceutiche Riunite SpA); Cyclopentanperhydrophenanthren-17beta-(3-furyl)-3-derivs. and pharmaceutical compsns. comprising same for the treatment of cardiovascular disorders. EP 0576915; JP 1994065284; US 5432169 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27462 (3S,5R,8R,9S,10S,13R,17R)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthrene-3,14-diol C23H34O3 详情 详情
(II) 12113 2-Bromo-1-ethoxyethyl ethyl ether; 2-Bromo-1,1-diethoxyethane; Bromoacetaldehyde diethylacetal 2032-35-1 C6H13BrO2 详情 详情
(III) 27463 (3S,5R,8R,9S,10S,13R,17R)-3-(2,2-diethoxyethoxy)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol C29H46O5 详情 详情
(IV) 27464 2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-17-(3-furyl)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]acetaldehyde C25H36O4 详情 详情
(V) 27465 (3S,5R,8R,9S,10S,13R,17R)-17-(3-furyl)-3-(2-hydroxyethoxy)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol C25H38O4 详情 详情
(VI) 12376 Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione 85-41-6 C8H5NO2 详情 详情
(VII) 27466 2-(2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-17-(3-furyl)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]ethyl)-1H-isoindole-1,3(2H)-dione C33H41NO5 详情 详情
(VIII) 27467 (3S,5R,8R,9S,10S,13R,17R)-3-(2-aminoethoxy)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol C25H39NO3 详情 详情
(IX) 10268 3,5-Dimethyl-1H-pyrazole-1-carboximidamide C6H10N4 详情 详情
Extended Information