Journal of Organic Chemistry p. 4243 - 4249 (1992)
Update date:2022-08-03
Topics:
Nagao, Yoshimitsu
Nagase, Yunosuke
Kumagai, Toshio
Matsunaga, Hiroshi
Abe, Takao
et al.
Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5.Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d).Compounds 17a,b were successfully converted to new, non-natural 1β-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.
View MoreContact:+86-571-87010026
Address:202, Zhenhua Road,
Shanghai Send Pharmaceutical Technology Co., Ltd.
website:http://www.shsendpharma.com
Contact:021-58088081, +8613585868794
Address::Room A601, Building 1,NO. 800 Qingdai Road Pudong District Shanghai,China
Cerametek Materials(ShenZhen)Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
Shijiazhuang Yunxuan Im&Export Co.,Ltd.
Contact:+86-311-83037514
Address:No.6 Hongbin Road
Wuhan Konberd Biotech Co., Ltd.
Contact:+86-27-87205925
Address:NO.666, Gaoxin Road, Eastlake High-tech zone
Doi:10.1021/jm301215e
(2013)Doi:10.1021/ic301834x
(2013)Doi:10.1021/ja3116718
(2013)Doi:10.1021/bm4009974
(2013)Doi:10.1039/DT9920001277
(1992)Doi:10.1134/S1070363212120055
(2012)