Capecitabine, R-340, Ro-09-1978, Xeloda
卡培他滨Chemical Name: 5'-Deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine; N-[1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamic acid pentyl ester
CAS No. 154361-50-9
项目整合开发状态: Launched-1998
项目研究机构: Chugai (Originator), Roche (Originator)
合成路线:The acetylation of 5'-deoxy-5-fluorocytidine (I) with acetic anhydride in dry pyridine gives 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine (II),which is condensed with pentyl chloroformate (III) by means of pyridine in dichromethane yielding 2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine (IV).Finally,this compound is deacetylated with NaOH in dichloromethane/water.The diacetylated cytidine (II) can also be obtained by condensation of 5-fluorocytosine (V) with 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose (VI) by means of trimethylchlorosilane in acetonitrile or HMDS and SnCl4 in dichloromethane..
📌 参考资料/链接：
参考文献标题:N-Oxycarbonyl substd.5'-deoxy-5-fluorocytidines
文献作者:Arasaki,M.; Ishitsuka,H.; Kurama,I.; Miwa,M.; Murasaki,C.; Shimma,N.; Umeda,I.(F.Hoffmann-La Roche AG)
参考来源:EP 0602454; JP 1994211891; US 5472949
📄 详细内容
合成路线:The acetylation of 5'-deoxy-5-fluorocytidine (I) with acetic anhydride in dry pyridine gives 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine (II),which is condensed with pentyl chloroformate (III) by means of pyridine in dichromethane yielding 2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine (IV).Finally,this compound is deacetylated with NaOH in dichloromethane/water.The diacetylated cytidine (II) can also be obtained by condensation of 5-fluorocytosine (V) with 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose (VI) by means of trimethylchlorosilane in acetonitrile or HMDS and SnCl4 in dichloromethane..
参考文献标题:Capecitabine
文献作者:Hoshi,A.; Castar,J.
参考来源:Drugs Fut 1996,21(4),358
合成路线:The acetylation of 5'-deoxy-5-fluorocytidine (I) with acetic anhydride in dry pyridine gives 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine (II),which is condensed with pentyl chloroformate (III) by means of pyridine in dichromethane yielding 2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine (IV).Finally,this compound is deacetylated with NaOH in dichloromethane/water.The diacetylated cytidine (II) can also be obtained by condensation of 5-fluorocytosine (V) with 1,2,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose (VI) by means of trimethylchlorosilane in acetonitrile or HMDS and SnCl4 in dichloromethane..
参考文献标题:The design and synthesis of a new tumor-selective fluoropyrimidine carbamate,capecitabine
文献作者:Shimma,N.; Umeda,I.; Arasaki,M.; Murasaki,C.; Masubuchi,K.; Kohchi,Y.; Miwa,M.; Ura,M.; Sawada,N.; Tahara,H.; Kuruma,I.; Horii,I.; Ishitsuka,H.
参考来源:Bioorg Med Chem Lett 2000,8(7),1697
产品链接: CAS No. 154361-50-9››