新产品编号:748795
Chemical Name: 3-[3,17beta-Dihydroxyestra-1(10),2,4-trien-17-yl]-2-propynoic acid cyclodec-5-en-3,7-diyn-1-ylmethyl ester
CAS No. 286428-06-6
项目整合开发状态: Biological Testing
项目研究机构: Beth Israel Deaconess Medical Center (Originator), Clemson University (Originator), Dana-Farber Cancer Institute (Originator), Harvard Medical School (Originator), Northwestern University (Originator)
合成路线:Ethynyl estradiol (I) was protected at the phenolic hydroxyl group as the silyl ether (II) by using triethylsilyl chloride and imidazole.The lithium acetylide derived from (II) was then carboxylated by a stream of CO2 to afford the propiolic acid derivative (III).Subsequent coupling of acid (III) with the cyclic enediine alcohol (IV) in the presence of EDC and DMAP furnished the silyl-protected ester (V).Finally,desilylation of (V) with either Bu4NF or HF穚yridine led to the target compound.
📌 参考资料/链接：
参考文献标题:Target-directed enediynes: Design estramycins
文献作者:Jones,G.B.; Hynd,G.; Wright,J.M.; Purohit,A.; Plourde,G.W.II.; Huber,R.S.; Mathews,J.E.; Li,A.; Kilgore,M.W.; Bubley,G.J.; Yancisin,M.; Brown,M.A.
参考来源:J Org Chem 2001,66(11),3688
📄 详细内容
合成路线:Ethynyl estradiol (I) was protected at the phenolic hydroxyl group as the silyl ether (II) by using triethylsilyl chloride and imidazole.The lithium acetylide derived from (II) was then carboxylated by a stream of CO2 to afford the propiolic acid derivative (III).Subsequent coupling of acid (III) with the cyclic enediine alcohol (IV) in the presence of EDC and DMAP furnished the silyl-protected ester (V).Finally,desilylation of (V) with either Bu4NF or HF穚yridine led to the target compound.
参考文献标题:Protein-degrading enediynes: Library screening of Bergman cycloaromatization products
文献作者:Jones,G.B.; Wright,J.M.; Hynd,G.; Wyatt,J.K.; Yancisin,M.; Brown,M.A.
参考来源:Org Lett 2000,2(13),1863