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项目整合精选>>>Etoposide, VP-16, VP-16-213, NSC-141540, EPEG, Etopophos, Lastet, Etosid, Vepeside, Etopol, Vepesid
Etoposide, VP-16, VP-16-213, NSC-141540, EPEG, Etopophos, Lastet, Etosid, Vepeside, Etopol, Vepesid
依托泊苷Chemical Name: 4'-Demethylepipodophyllotoxin 4-(4,6-O-ethylidene-beta-D-glucopyranoside); [5R-[5alpha,5abeta,8aalpha,9beta(R*)]]-9-[(4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
CAS No. 33419-42-0
项目整合开发状态: Launched-1980
项目研究机构: Novartis (Originator), National Cancer Institute (Not Determined), Nippon Kayaku (Not Determined), Amgen (Licensee), Bristol-Myers Squibb (Licensee), Sparta (Licensee), Wyeth Pharmaceuticals (Licensee)
合成路线:By reaction of 4,6-O-ethylidene-2,3-di-O-acetyl-beta-D-glucopyranose (I) and 4'-benzyloxycarbonyl-4'-demethyl-epipodophyllotoxin (II) in the presence of boron trifluoride etherate to give the compound (III),which is treated with Zn(OAc)2 and NaOAc followed by reduction with Pd-C.
📌 参考资料/链接：
参考文献标题:Etoposide
文献作者:Cabanillas,F.
参考来源:Drugs Fut 1979,4(4),257
📄 详细内容
合成路线:The condensation of dibenzyl-sugar (II) with 4'-demethyl-epipodophyllotoxin (I) by means of BF3稥t2O in acetonitrile gives a mixture of the alpha and beta coupled products (IV) + (III),which by crystallization in dichloromethane/methanol afforded pure diastereomer beta (III).Finally this compound is debenzylated by hydrogenolysis with H2 over Pd/C in THF.
参考文献标题:A crystallization-induced steroselective glycosidation reaction in the synthesis of the anticancer drug etoposide
文献作者:Silverberg,L.J.; Kelly,S.; Vemishetti,P.; Vipond,D.H.; Gibson,F.S.; Harrison,B.; Spector,R.; Dillon,J.L.
参考来源:Org Lett 2000,2(21),3281
合成路线:By reaction of 4,6-O-ethylidene-2,3-di-O-acetyl-beta-D-glucopyranose (I) and 4'-benzyloxycarbonyl-4'-demethyl-epipodophyllotoxin (II) in the presence of boron trifluoride etherate to give the compound (III),which is treated with Zn(OAc)2 and NaOAc followed by reduction with Pd-C.
参考文献标题:Verhafren zur Herstellung von Glucosiden
文献作者:Kuhn,M.; et al.
参考来源:AT 303270B; AT 319971B; CH 514578; NL 6901619
产品链接: CAS No. 33419-42-0››