合成路线:This compound can be prepared in several different ways:1) The Grignard reaction of 3-methoxy-17beta-hydroxyestra-1,3,5(10)-trien-16-one (I) with ethyl magnesium bromide (A) in ether gives 3-methoxy-16alpha-ethylestra-1,3,5(10)-trien-16beta,17beta-diol (II),which by a Birch reduction with Li in liquid NH3 is converted into 16alpha-ethyl-16beta,17beta-dihydroxyestr4-en-3-one (III).The dehydration of (III) with H2SO4 in methanol yields 16-ethylestr-4-en-3,17-dione (VI),which by reaction with triethyl orthoformate in dioxane catalyzed by p-toluenesulfonic acid is converted into 3-ethoxy-16beta-ethylestra-3,5-diene-17-one (V).The reduction of (V) with NaBH4 in methanol affords 3-ethoxy-16beta-ethylestra-3,5-diene-17-ol (VI),which is finally hydrolyzed with HCl in methanol.
参考文献标题:
文献作者:Hiraga,K.; et al.
参考来源:JP 7434982
合成路线:The oxidation of 19-hydroxy-16beta-ethyl-17beta-acetoxyandrost-4-en-3-one (XIII) with CrO3 and H2SO4 gives the corresponding carboxylic acid (XIV),which is decarboxylated with HCl in refluxing methanol affording 16beta-ethyl-17beta-acetoxyestra-4-en-3-one (XV).Finally this compound is hydrolyzed with KOH in refluxing methano.l
参考文献标题:
文献作者:Yoshioka,K.; et al.
参考来源:JP 7434983
合成路线:This compound can be prepared in several different ways:1) The Grignard reaction of 3-methoxy-17beta-hydroxyestra-1,3,5(10)-trien-16-one (I) with ethyl magnesium bromide (A) in ether gives 3-methoxy-16alpha-ethylestra-1,3,5(10)-trien-16beta,17beta-diol (II),which by a Birch reduction with Li in liquid NH3 is converted into 16alpha-ethyl-16beta,17beta-dihydroxyestr4-en-3-one (III).The dehydration of (III) with H2SO4 in methanol yields 16-ethylestr-4-en-3,17-dione (VI),which by reaction with triethyl orthoformate in dioxane catalyzed by p-toluenesulfonic acid is converted into 3-ethoxy-16beta-ethylestra-3,5-diene-17-one (V).The reduction of (V) with NaBH4 in methanol affords 3-ethoxy-16beta-ethylestra-3,5-diene-17-ol (VI),which is finally hydrolyzed with HCl in methanol.
合成路线:The Grignard reaction of 3-methoxy-17beta-hydroxyestra-1,3,5(10)-trien-16-one (I) with ethyl magnesium bromide (A) in ether gives 3-methoxy-16alpha-ethylestra-1,3,5(10)-trien-16beta,17beta-diol (II),which by dehydration with H2SO4 in methanol gives 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17-one (VII),which is reduced with NaBH4 in methanol yielding 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol (VIII).Finally this compound is submitted to a Birch reduction with Li in liquid NH3.
合成路线:The methylation of estrone (IX) with methyl sulfate gives estrone 3-methyl ether (X),which is acetylated with ethyl acetate and sodium methoxide in DMSO yielding 16-acetylestrone-3-methyl ether (XI).The reaction of (XI) with acetic anhydride in pyridine at 65 C gives 16-(1'-acetoxyethylidene)estrone-3-methyl ether (XII),which is finally reduced with H2 over Raney-Ni in ethanol affording 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol (VIII).Finally this compound is submitted to a Birch reduction with Li in liquid NH3.
合成路线:The oxidation of 19-hydroxy-16beta-ethyl-17beta-acetoxyandrost-4-en-3-one (XIII) with CrO3 and H2SO4 gives the corresponding carboxylic acid (XIV),which is decarboxylated with HCl in refluxing methanol affording 16beta-ethyl-17beta-acetoxyestra-4-en-3-one (XV).Finally this compound is hydrolyzed with KOH in refluxing methano.l
参考文献标题:Oxendolone
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Thorpe,P.J.
参考来源:Drugs Fut 1980,5(9),441
合成路线:The Grignard reaction of 3-methoxy-17beta-hydroxyestra-1,3,5(10)-trien-16-one (I) with ethyl magnesium bromide (A) in ether gives 3-methoxy-16alpha-ethylestra-1,3,5(10)-trien-16beta,17beta-diol (II),which by dehydration with H2SO4 in methanol gives 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17-one (VII),which is reduced with NaBH4 in methanol yielding 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol (VIII).Finally this compound is submitted to a Birch reduction with Li in liquid NH3.
参考文献标题:A stereoselective nuclear magnetic resonance spectral study of four epimeric 17-hidroxy-16-ethylestranes
文献作者:Goto,G.; et al.
参考来源:Chem Pharm Bull 1977,25(6),1295-1301
合成路线:The Grignard reaction of 3-methoxy-17beta-hydroxyestra-1,3,5(10)-trien-16-one (I) with ethyl magnesium bromide (A) in ether gives 3-methoxy-16alpha-ethylestra-1,3,5(10)-trien-16beta,17beta-diol (II),which by dehydration with H2SO4 in methanol gives 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17-one (VII),which is reduced with NaBH4 in methanol yielding 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol (VIII).Finally this compound is submitted to a Birch reduction with Li in liquid NH3.
参考文献标题:Synthesis and antiandrogenic activity of 16B-substituted-17B-hydroxysteroids
文献作者:Goto,G.
参考来源:Ibid 1978,26(6),1718-1728
合成路线:The methylation of estrone (IX) with methyl sulfate gives estrone 3-methyl ether (X),which is acetylated with ethyl acetate and sodium methoxide in DMSO yielding 16-acetylestrone-3-methyl ether (XI).The reaction of (XI) with acetic anhydride in pyridine at 65 C gives 16-(1'-acetoxyethylidene)estrone-3-methyl ether (XII),which is finally reduced with H2 over Raney-Ni in ethanol affording 16beta-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol (VIII).Finally this compound is submitted to a Birch reduction with Li in liquid NH3.
参考文献标题:Studies and antiandrogenic activity of 16B-ethyl-19-nortesterone
文献作者:Yoshioka,K.; et al.
参考来源:Ibid 1975,23(12),3203-3207
产品链接: CAS No. 33765-68-3››