新产品编号:1259781
Chemical Name: 4(S)-(Benzyloxycarbonyl-L-leucyl-L-phenylalanylamino)-6-carbamoyl-2(E)-hexenoic acid ethyl ester
项目整合开发状态: Biological Testing
项目研究机构: Agouron (Originator)
合成路线:The condensation of the protected L-glutamine (I) with N,O-dimethylhydroxylamine (II) by means of isobutyl chloroformate and NMM in dichloromethane gives the methoxyamide (III),which is reduced with DIBAL in THF to the aldehyde (IV).The condensation of (IV) with phosphonate (V) by means of NaN(SiMe3)2 in THF yields the carbamoylhexenoate (VI),which is selectively deprotected with HCl in dioxane and condensed with the dipeptide (VII) by means of HOBT,NMM and EDC in dichloromethane to afford the tritylated target compound (VIII).Finally,the trityl group of (VIII) is eliminated with TFA and Et3SiH in dichloromethane.
📌 参考资料/链接：
参考文献标题:Structure-based design,synthesis,and biological evaluation of irreversible human rhinovirus 3C protease inhibitors.1.Michael acceptor structure-activity studies
文献作者:Dragovich,P.S.; Webber,S.E.; Babine,R.E.; Fuhrman,S.A.; Patick,A.K.; Matthews,D.A.; Lee,C.A.; Reich,S.H.; Prins,T.J.; Marakovits,J.T.; Littlefield,E.S.; Zhou,R.; Tikhe,J.; Ford,C.E.; Wallace,M.B.; Meador,J.W.III; Ferre,R.A.; et al.
参考来源:J Med Chem 1998,41(15),2806