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Azidothymidine phosphonate, Nicavir, Phosphazid, phAZT

3'-叠氮-3'-脱氧-5'-O-(羟基磷羧基酰)胸苷Chemical Name: 3'-Azido-3'-deoxy-5'-O-(hydroxyphosphonoyl)thymidine; 3'-Azido-3'-deoxythymidine 5'-(hydrogen phosphonate)
CAS No. 124930-59-2
项目整合开发状态: Phase I
项目研究机构: Russian Academy of Sciences (Originator)
合成路线:The title compound was obtained from 3'-azido-3'-deoxythymidine (I) either by treatment with tri-n-butylammonium phosphite and DCC in pyridine or by treatment with phosphorus trichloride in the presence of imidazole and Et3N in acetonitrile or in the presence of triethyl phosphate,followed by aqueous hydrolysis.
📌 参考资料/链接:
参考文献标题:5'-Hydrogenphosphonates and 5'-methylphosphonates of sugar modified nucleosides,compsns.and uses thereof
文献作者:Krayevsky,A.A.; Tarussova,N.B.; Watanabe,K.A.; Matulic-Adamic,J.(Sloan-Kettering Institute)
参考来源:WO 9119727

📄 详细内容


合成路线:The title compound was obtained from 3'-azido-3'-deoxythymidine (I) either by treatment with tri-n-butylammonium phosphite and DCC in pyridine or by treatment with phosphorus trichloride in the presence of imidazole and Et3N in acetonitrile or in the presence of triethyl phosphate,followed by aqueous hydrolysis.

参考文献标题:Nucleoside 5'-phosphonates: Synthesis,anti-HIV activities and reactions with DNA polymerases
文献作者:Dyatkina,N.; et al.
参考来源:Antivir Res 1993,20(Suppl.1),Abst 24


合成路线:The title compound was obtained from 3'-azido-3'-deoxythymidine (I) either by treatment with tri-n-butylammonium phosphite and DCC in pyridine or by treatment with phosphorus trichloride in the presence of imidazole and Et3N in acetonitrile or in the presence of triethyl phosphate,followed by aqueous hydrolysis.

合成路线:3'-azido-3'-deoxythimidine (II) was phosphitylated with phosphorus trichloride in triethyl phosphate to yield the corresponding hydrogen phosphonate (III).Subsequent coupling of (III) with 1,2-dipalmitoylglycerol (IV) by means of pivaloyl chloride in pyridine produced phosphite ester (V),which was finally oxidized to the title phosphate with ethanolic iodine.
参考文献标题:Lymphatic targeting of anti-HIV nucleosides: Distribution of 3'-azido-3'-deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZdU) after administration of dipalmitoylphosphatidyl prodrugs to mice
文献作者:Manouilov,K.K.; Fedorov,I.I.; Boudinot,F.D.; White,C.A.; Kotra,L.P.; Schinazi,R.F.; Hong,C.I.; Chu,C.K.
参考来源:Antivir Chem Chemother 1995,6(4),230


产品链接: CAS No. 124930-59-2››