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项目整合精选>>>Azidothymidine, Zidovudine, Cpd S, AZT, BW-A509U, AZTEC, Retrovir
Azidothymidine, Zidovudine, Cpd S, AZT, BW-A509U, AZTEC, Retrovir
齐多夫定Chemical Name: 3'-Azido-3'-deoxythymidine
CAS No. 30516-87-1
项目整合开发状态: Launched-1987
项目研究机构: GlaxoSmithKline (Originator)
合成路线:1) The mesylation of 5'-O-tritylthymidine with mesyl chloride gives the corresponding 3'-O-mesyl derivative (II),which is cyclized by means of potassium phthalimide (III) in hot DMF water,yielding 5'-O-trityl-2,3'-anhydrothymidine (IV).The reaction of (IV) with sodium azide in refluxing DMF - water affords 5'-O-trityl-3'-azido-3'-deoxy thymidine (V),which is finally deprotected with 80% aqueous acetic acid at 100 C.
合成路线:2) The anhydrization of thymidine (VI) with 2-chloro-1,2-difluorotriethylamine in hot DMF gives 2,3'-anhydrothymidine (VII),which is then treated with lithium azide and NH4Cl in hot DMF.
📌 参考资料/链接：
参考文献标题:BW-A 509 U
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1986,11(12),1017
📄 详细内容
合成路线:1) The mesylation of 5'-O-tritylthymidine with mesyl chloride gives the corresponding 3'-O-mesyl derivative (II),which is cyclized by means of potassium phthalimide (III) in hot DMF water,yielding 5'-O-trityl-2,3'-anhydrothymidine (IV).The reaction of (IV) with sodium azide in refluxing DMF - water affords 5'-O-trityl-3'-azido-3'-deoxy thymidine (V),which is finally deprotected with 80% aqueous acetic acid at 100 C.
合成路线:2) The anhydrization of thymidine (VI) with 2-chloro-1,2-difluorotriethylamine in hot DMF gives 2,3'-anhydrothymidine (VII),which is then treated with lithium azide and NH4Cl in hot DMF.
参考文献标题:Nucleotide synthesis.IV.Phosphorylated 3'-amino-3'-deoxythymidine and 5'-amino-5'-deoxythymidine and derivatives
文献作者:Glinski,R.P.; et al.
参考来源:J Org Chem 1973,38(25),4299
产品链接: CAS No. 30516-87-1››