【药物名称】bis(tBuSATE)AZT-MP, UA-428
化学结构式(Chemical Structure):
参考文献No.556857
标题:Synthesis of the tBuSATE pronucleotide of AZT by two different synthetic approaches
作者:Lannuzel, M.; Egron, D.; Imbach, J.L.; Gosselin, G.; Perigaud, C.
来源:Nucleosides Nucleotides 1999,18(4-5),1001
合成路线图解说明:

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.

合成路线图解说明:

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.

参考文献No.556862
标题:Synthesis, descomposition pathways and "in vitro" evaluation of bioreversible phosphotriesters of AZT
作者:Lefebvre, I.; et al.
来源:Nucleosides Nucleotides 1995,14(3-5),763
合成路线图解说明:

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No.556863
标题:Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: Intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate
作者:Lefebvre, I.; Perigaud, C.; Pompon, A.; Aubertin, A.M.; Girardet, J.L.; Kirn, A.; Gosselin, G.; Imbach, J.L.
来源:J Med Chem 1995,38(20),3941
合成路线图解说明:

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.

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