bis(tBuSATE)AZT-MP, UA-428
Chemical Name: 3'-Azido-5'-O-[bis[2-(S-pivaloylsulfanyl)ethoxy]phosphoryl]-3'-deoxythymidine
CAS No. 168777-50-2
项目整合开发状态: Preclinical
项目研究机构: Katholieke Universiteit Leuven (Originator), Universit?Montpellier II (Originator)
合成路线:The esterification of 2,2-dimethyl-thiopropionic acid (I) with 2-iodoethanol (II) and DBU in toluene gives the corresponding thioester (III),which is condensed with diisopropylamidophosphoryl dichloride (IV) by means of TEA in THF to afford the phosphoramidite (V).Finally,this compound is condensed with AZT (VI) by means of 1H-tetrazole and MCPBA or 1H-tetrazole and tert-butyl peroxide,both cases in THF.
合成路线:The phosphorylation of AZT (VI) with POCl3 trimethyl phosphate gives the 5'-O-phosphate (VII),which is then condensed with the previously described thioester (III) by means of Tps-Cl in pyridine.
📌 参考资料/链接：
参考文献标题:Synthesis of the tBuSATE pronucleotide of AZT by two different synthetic approaches
文献作者:Lannuzel,M.; Egron,D.; Imbach,J.L.; Gosselin,G.; Perigaud,C.
参考来源:Nucleosides Nucleotides 1999,18(4-5),1001
📄 详细内容
合成路线:The esterification of 2,2-dimethyl-thiopropionic acid (I) with 2-iodoethanol (II) and DBU in toluene gives the corresponding thioester (III),which is condensed with diisopropylamidophosphoryl dichloride (IV) by means of TEA in THF to afford the phosphoramidite (V).Finally,this compound is condensed with AZT (VI) by means of 1H-tetrazole and MCPBA or 1H-tetrazole and tert-butyl peroxide,both cases in THF.
参考文献标题:Synthesis,descomposition pathways and "in vitro" evaluation of bioreversible phosphotriesters of AZT
文献作者:Lefebvre,I.; et al.
参考来源:Nucleosides Nucleotides 1995,14(3-5),763
合成路线:The esterification of 2,2-dimethyl-thiopropionic acid (I) with 2-iodoethanol (II) and DBU in toluene gives the corresponding thioester (III),which is condensed with diisopropylamidophosphoryl dichloride (IV) by means of TEA in THF to afford the phosphoramidite (V).Finally,this compound is condensed with AZT (VI) by means of 1H-tetrazole and MCPBA or 1H-tetrazole and tert-butyl peroxide,both cases in THF.
参考文献标题:Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: Intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate
文献作者:Lefebvre,I.; Perigaud,C.; Pompon,A.; Aubertin,A.M.; Girardet,J.L.; Kirn,A.; Gosselin,G.; Imbach,J.L.
参考来源:J Med Chem 1995,38(20),3941