Tetrahedron Letters p. 221 - 224 (1998)
Update date:2022-07-31
Topics:
Shreder, Kevin
Zhang, Li
Goodman, Murray
The synthesis of a constrained, piperazinone analog of Leu-enkephalin is presented. A key step in this synthesis was the use of the secondary amine, Boc-Tyr(OtBu)Ψ[CH2NH]Gly-OMe, to ring open the β-lactone of Z-protected L-serine (the Vederas lactone). The resulting free acid was then coupled to H-Phe-Leu-OtBu in a one-pot fashion using standard carbodiimide coupling conditions. This linear precursor cyclized upon hydrogenolysis of the Z group to form the N4-substituted, 6-carboxy-derived piperazinone (5). Deprotection of compound 5 using 1:1 TFA:CH2Cl2 yielded the target compound 1.
View MoreJintan City Mego Chemical Co., Ltd
Contact:+86-0519-82814387
Address:23# Dengguan Town, Jintan, Jiangsu Province, China
website:http://www.uvchemkeys.com
Contact:0086-021-58785816
Address:RM2607 Building No.1 Guosheng, Lane 388, Zhongjiang Road, Putuo District, Shanghai 200062 China
Contact:021-36356756
Address:Room601,Building No.14,280 Yangcheng Road,Shanghai
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
website:http://www.hybio.com.cn
Contact:+86 755 26588093
Address:No.9 Linkong West Street, Hengdian Street, Huangpi District, Wuhan City, China.
Doi:10.1248/cpb.46.79
(1998)Doi:10.1002/(sici)1521-3749(199803)624:3<399::aid-zaac399>3.0.co;2-7
(1998)Doi:10.1021/acs.orglett.0c02286
(2020)Doi:10.1016/S0040-4039(00)86253-X
(1983)Doi:10.1016/j.bmcl.2008.08.005
(2008)Doi:10.1021/ja00241a073
(1987)