L-beta-BV-OddU, BCH-2639
Chemical Name: 5-[(E)-2-Bromovinyl]-1-[2(S)-(hydroxymethyl)-1,3-dioxolan-4(S)-yl]pyrimidine-2,4(1H,3H)-dione; 5-[(E)-2-Bromovinyl)-1-[2(S)-(hydroxymethyl)-1,3-dioxolan-4(S)-yl]uracil
CAS No. 161105-93-7
项目整合开发状态: Biological Testing
项目研究机构: Shire BioChem (Originator), University of Georgia (Originator), Yale University (Originator)
合成路线:The condensation of the chiral dioxolane (I) with 5(E)-(2-bromovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II),which is purified by chromatography.Finally,this compound is deprotected by means of TBAF in acetonitrile.(1,2)
📌 参考资料/链接：
参考文献标题:5-(E)-Bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use
文献作者:Chu,C.K.; Cheng,Y.-C.; Li,L.; Chai,Y.(University of Georgia; Yale University)
参考来源:CA 2378370; EP 1204415; US 6653318; WO 0106986
📄 详细内容
合成路线:Hydrogenolysis of benzyl ether (I) in the presence of Pd/C afforded dioxolane alcohol (II),which was acetylated with Ac2O and pyridine to give diacetate (III).Subsequent condensation of (III) with the silylated (2-bromovinyl)uracil (IV) led to a diastereomeric mixture of nucleosides (V) and (VI).After chromatographic isolation of the desired isomer (V),hydrolysis of the acetate ester using K2CO3 in MeOH yielded the title compound.
参考文献标题:Inhibitory activities of herpes simplex viruses type 1 and 2 and human cytomegalovirus by stereoisomers of 2'-deoxy-3'-oxa-5(E)-(bromovinyl)uridines and their 4'-thio analogues
文献作者:Dixit,D.M.; Wang,W.; Yuen,L.; Jin,H.; Bednarski,K.; Evans,C.A.; Mansour,T.S.
参考来源:Bioorg Med Chem Lett 1994,4(22),2667
合成路线:The condensation of the chiral dioxolane (I) with 5(E)-(2-bromovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II),which is purified by chromatography.Finally,this compound is deprotected by means of TBAF in acetonitrile.(1,2)
合成路线:The condensation of the chiral dioxolane (I) with 5(E)-(2-chlorovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II) that is purified by chromatography.Finally,this compound is deprotected by means of TBAF in acetonitrile.
合成路线:The condensation of the chiral dioxolane (I) with 5(E)-(2-iodovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II),which is purified by chromatography.Finally,this compound is deprotected by means of TBAF in acetonitrile.
参考文献标题:Structure-activity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses
文献作者:Choi,Y.; Li,L.; Grill,S.; Gullen,E.; Lee,C.S.; Gumina,G.; Tsujii,E.; Cheng,Y.-C.; Chu,C.K.
参考来源:J Med Chem 2000,43(13),2538