Steroids p. 867 - 872 (2005)
Update date:2022-08-17
Topics:
Milisavljevic, Smiljka S.
Wurst, Klaus
Laus, Gerhard
Vukicevic, Mirjana D.
Vukicevic, Rastko D.
Four 5,6-unsaturated steroids - 3β-chlorocholest-5-ene (1a), cholesterol (1b) and its acetate (1c) and benzoate (1d) - were subjected to constant current electrolysis (50 mA, 2 F mol-1) in an electrolytic cell divided by a ceramic membrane, using a platinum foil as the anode and a graphite stick as the cathode. When electrolysis was carried out in a solution of tetraethylammonium bromide in aprotic solvents (dichloromethane, acetonitrile or acetic anhydride), the addition of electrochemically-generated elemental bromine onto the double bond of the cholesterol derivatives gave their corresponding 5α,6β-dibromosteroids - 3β-chloro-5α, 6β-dibromocholestane (2a), 5α,6β-dibromocholestan-3β-ol (2b), 5α,6β-dibromocholestan-3β-yl acetate (2c) and 5α,6β-dibromocholestan-3β-yl benzoate (2d) - as the sole products, and in good yields (58-91%). However, the electrolysis of steroids 1a-c in a solution of tetraethylammonium bromide with methanol as the solvent proceeded to give, in addition to dibromides 2a-c, the corresponding diastereomeric pairs of 5-bromo-6-methoxysteroids: 5α-bromo-3β- chloro-6β-methoxycholestane (3a) and 5β-bromo-3β-chloro-6α- methoxycholestane (4a), 5α-bromo-6β-methoxycholestan-3β-ol (3b) and 5β-bromo-6α-methoxycholestan-3β-ol (4b) and 5α-bromo-6β-methoxycholestan-3β-yl acetate (3c) and 5α-bromo-6β-methoxycholestan-3β-yl acetate (4c). The benzoate 1d was not soluble enough in methanol, even with heating. The products were characterized by physical and spectral data (IR, 1H NMR and 13C NMR). Single crystal X-ray structure determinations of compounds 2a and 3a are also reported.
View MoreTaizhou Chemedir Biopharm-tech Co., Ltd
Contact:+86 523 86200218
Address:G09, No. 1 Avenue China Medical City, Taizhou,Jiangsu, China
Arshine Pharmaceutical Co., Limited
website:http://www.cnarshine.com
Contact:0731-88503671
Address:Room 1109.Block C3, Lugu Enterprise Plaza,No.27 Wenxuan Road,Changsha National Hi-Tech Industrial Development Zone,Hunan ,P.R.China
Henan Tianfu Chemical Co., Ltd.
website:http://www.tianfuchem.com
Contact:86-371-55170693/55170694
Address:Zhengzhou International Trade New Territory,Jinshui District,Zhengzhou ,China
TANGSHAN SANJIANG CHEMICAL CO.,LTD
Contact:86-315-2239987
Address:NANPU ECNOMIC DEVELOPMENT ZONE,TANGSHAN ,CHINA
Shanghai Yuanye Bio-Technology Co., Ltd.
website:http://www.shyuanye.com
Contact:+86-21-61845781
Address:Building 6, No. 465, Changta Road,Songjiang District,Shanghai,China
Doi:10.1524/zpch.2000.214.11.1479
(2000)Doi:10.1002/psc.3245
(2020)Doi:10.14233/ajchem.2020.22750
(2020)Doi:10.1039/c39740000298
(1974)Doi:10.1007/BF01434104
(1932)Doi:10.1039/c9cc07439b
(2020)