Journal of the Chemical Society. Perkin Transactions 1 (2001) p. 1587 - 1594 (2000)
Update date:2022-08-05
Topics:
Michalak, Karol
Stepanenko, Wiaczeslaw
Wicha, Jerzy
Reduction reactions of chplest-4-en-3-one derivatives bearing the phenylsulfonyl or phenylsulfanyl group at C-4 with various metal hydrides are studied. Lithium aluminohydride reduction of 4-(phenylsulfonyl)cholest-4-en-3β-ol 13a and 4-(phenylsulfonyl)cholest-4-en-3α-ol 15a occurs with saturation of the double bond and deoxygenation to give 4β-phenylsulfonyl-5β-cholestane 8 and 4α-phenylsulfonyl-5α-cholestane 7a, respectively. Reduction of 4-(phenylsulfonyl)cholest-4-en-3-one 2 with lithium aluminohydride yields compound 8. Reduction of compounds 2, 13a and 15a with other metal hydrides affords mixtures of diastereomeric products. Metal hydride reductions of 4-(phenylsulfanyl)cholest-4-en-3-one 1 affect the carbonyl group only. Catalytic hydrogenation of compound 2 gives a mixture of 5α- and 5β- dihydro derivatives. Mechanistic and stereochemical aspects of the reduction reactions are discussed. The Royal Society of Chemistry 2000.
View MoreContact:86-571-61063068
Address:LINAN
Wuxi Forest Biological Co.,Ltd
Contact:+86-510-81602300
Address:Room 317,Building D, No.159 middle Chengjiang Road,Jiangyin Wuxi city.
Dezhou Longteng Chemical Co., Ltd.
website:http://www.sodium-methoxide.cn/
Contact:0086-18866052283
Address:Xinhua Industrial Zone, Dezhou City, Shandong Province, China
SICHUAN TONGSHENG AMINOACID CO.LTD
website:http://www.aminoacid.cc
Contact:86-838-2274206/2850606
Address:Room 1-11-1,No.19 of North TianShan Road,Deyang,Sichuan China
Hangzhou Bayee Chemical Co.,Ltd.
Contact:+86-571-86990109
Address:No.380, Jiangnan Auenue, Binjiang District, Hangzhou, China
Doi:10.1021/jo402527w
(2014)Doi:10.1021/jo000071g
(2000)Doi:10.1039/c8nj02818d
(2018)Doi:10.1016/S0040-4039(00)77868-3
(1976)Doi:10.1016/S0040-4020(00)00283-0
(2000)Doi:10.1039/c39830001158
(1983)