新产品编号:1261363
Chemical Name: 6-Carbamoyl-4(S)-[N-(Cyclopentylsulfanylcarbonylamino)-L-(3-methyl)valyl-L-(4-methyl)phenylalanylamino]-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 reaction 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 yielding the glutaminal (IV).The condensation of (IV) with phosphonate (V) by means of NaN(SiMe3)2 in THF affords the carbamoylhexenoate (VI),which is deprotected with TFA and HCl and condensed with N-(tert-butoxycabonyl)-4-methyl-L-phenylalanine (VII) by means of HOBT,NMM and EDC in dichloromethane to give the dipeptide (VIII),which is finally deprotected with HCl and condensed with N-(cyclopentylsulfanylcarbonyl)-L-tert-leucine (IX) by means of HOBT as before.
📌 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.2.Peptide 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.; Reich,S.H.; Marakovits,J.T.; Prins,T.J.; Zhou,R.; Tikhe,J.; Littlefield,E.S.; Bleckman,T.M.; Wallace,M.B.; Little,T.L.; Ford,C.E.; et al.
参考来源:J Med Chem 1998,41(15),2819