新产品编号:1832465
Chemical Name: 7alpha-[10-(N-Butyl-N-methylcarbamoyl)decyl]-3-hydroxy-19-nor-17alpha-pregna-1,3,5(10)-triene-21,17-carbolactone
项目整合开发状态: Biological Testing
项目研究机构: Universit?Laval (Originator)
合成路线:The known estradiol derivative (I) was oxidized with Jones reagent to give the keto acid (II).After activation of (II) as the mixed anhydride with isobutyl chloroformate,condensation with N-butyl-N-methylamine yielded amide (III).Addition of the lithium acetylide of 2-(propinyloxy)tetrahydropyran (IV) to the keto group of (III) furnished the corresponding propargyl alcohol (V) with concomitant cleavage of the benzoate ester.The triple bond of (V) was then subjected to catalytic hydrogenation using a mixture of Pd/C and Pd/CaCO3 as the catalyst to produce the saturated compound (VI).After cleavage of the tetrahydropyranyl protecting group of (VI) with amberlyst-15 ion-exchange acid resin in MeOH,the deprotected alcohol was oxidized and cyclized with Jones reagent to yield the desired gamma-lactone
📌 参考资料/链接:
参考文献标题:N-Butyl-N-methyl-11-(3'-hydroxy-21',17'-carbolactone-19'-nor-17'alpha-pregna-1',3',5' (10')-trien-7'alpha-yl)-undecanamide: an inhibitor of type 2 17beta-hydroxysteroid dehydrogenase that does not have oestrogenic or androgenic activity
文献作者:Sam,K.M.; Labrie,F.; Poirier,D.
参考来源:Eur J Med Chem 2000,35(2),217