合成路线:Prasterone can be obtained by two related ways:1) The acetylation of cholesterol (I) with refluxing acetic anhydride gives the corresponding acetate (II),which is brominated with Br2 in acetic acid to the dibromide (III).The oxidation of (III) with CrO3 in acetic acid followed by debromination with Zn in the same solvent and treatment with semicarbazide and sodium acetate in ethanol/water affords 3beta-acetoxyandrost-5-en-17-one semicarbazone (IV),which is finally hydrolyzed with 5N H2SO4 in refluxing ethanol.2) The partial silylation of androst-5-ene-3beta,17beta-diol (V) with tert-butyldimethylsilyl chloride and imidazole in DMF yields the 3beta-silyloxy derivative (VI),which is oxidized with CrO3-pyridine complex in pyridine affording 3-(tert-butyldimethylsilyloxy)androst-5-en-17-one (VII).Finally,this compound is deprotected with hot acetic acid/water/THF or with tetrabutylammonium fluoride in THF.
参考文献标题:The preparation of dehydroandrosterone from cholesterol
文献作者:Fernholz,E.; Wallis,E.S.
参考来源:J Am Chem Soc 1935,571504-6
合成路线:Prasterone can be obtained by two related ways:1) The acetylation of cholesterol (I) with refluxing acetic anhydride gives the corresponding acetate (II),which is brominated with Br2 in acetic acid to the dibromide (III).The oxidation of (III) with CrO3 in acetic acid followed by debromination with Zn in the same solvent and treatment with semicarbazide and sodium acetate in ethanol/water affords 3beta-acetoxyandrost-5-en-17-one semicarbazone (IV),which is finally hydrolyzed with 5N H2SO4 in refluxing ethanol.2) The partial silylation of androst-5-ene-3beta,17beta-diol (V) with tert-butyldimethylsilyl chloride and imidazole in DMF yields the 3beta-silyloxy derivative (VI),which is oxidized with CrO3-pyridine complex in pyridine affording 3-(tert-butyldimethylsilyloxy)androst-5-en-17-one (VII).Finally,this compound is deprotected with hot acetic acid/water/THF or with tetrabutylammonium fluoride in THF.
参考文献标题:The constitution of dehydro-androsterone and its preparation from cholesterol
文献作者:Fernholz,E.; Wallis,E.S.
参考来源:J Am Chem Soc 1935,571379-80
合成路线:Prasterone can be obtained by two related ways:1) The acetylation of cholesterol (I) with refluxing acetic anhydride gives the corresponding acetate (II),which is brominated with Br2 in acetic acid to the dibromide (III).The oxidation of (III) with CrO3 in acetic acid followed by debromination with Zn in the same solvent and treatment with semicarbazide and sodium acetate in ethanol/water affords 3beta-acetoxyandrost-5-en-17-one semicarbazone (IV),which is finally hydrolyzed with 5N H2SO4 in refluxing ethanol.2) The partial silylation of androst-5-ene-3beta,17beta-diol (V) with tert-butyldimethylsilyl chloride and imidazole in DMF yields the 3beta-silyloxy derivative (VI),which is oxidized with CrO3-pyridine complex in pyridine affording 3-(tert-butyldimethylsilyloxy)androst-5-en-17-one (VII).Finally,this compound is deprotected with hot acetic acid/water/THF or with tetrabutylammonium fluoride in THF.
参考文献标题:Convenient,high yield conversion of androst-5-ene-3beta,17beta-diol to dehydroisoandrosterone
文献作者:Hosoda,H.; Fukushima,D.K.; Fishman,J.
参考来源:J Org Chem 1973,38(24),4209-11
合成路线:Prasterone can be obtained by two related ways:1) The acetylation of cholesterol (I) with refluxing acetic anhydride gives the corresponding acetate (II),which is brominated with Br2 in acetic acid to the dibromide (III).The oxidation of (III) with CrO3 in acetic acid followed by debromination with Zn in the same solvent and treatment with semicarbazide and sodium acetate in ethanol/water affords 3beta-acetoxyandrost-5-en-17-one semicarbazone (IV),which is finally hydrolyzed with 5N H2SO4 in refluxing ethanol.2) The partial silylation of androst-5-ene-3beta,17beta-diol (V) with tert-butyldimethylsilyl chloride and imidazole in DMF yields the 3beta-silyloxy derivative (VI),which is oxidized with CrO3-pyridine complex in pyridine affording 3-(tert-butyldimethylsilyloxy)androst-5-en-17-one (VII).Finally,this compound is deprotected with hot acetic acid/water/THF or with tetrabutylammonium fluoride in THF.
参考文献标题:Sexual hormones: Synthetic preparation of the male sexual hormones trans-dehydroandrosterone and androstene-3,17-dione
文献作者:Ruzicka,L.; Wettstein,A.
参考来源:Helv Chim Acta 1935,18986-95
产品链接: CAS No. 53-43-0››