新产品编号:2439953

Chemical Name: 5'-O-[[4-[2(S)-Amino-2-carbamoylethyl]phenoxy][2-(2,2-dimethylpropionylsulfanyl)ethoxy]phosphoryl]-3'-azido-3'-deoxythymidine
项目整合开发状态: Biological Testing
项目研究机构: CNRS (Originator), INSERM (Originator)
合成路线:N-Boc-L-Tyrosine (I) methyl ester is treated with methanolic ammonia to provide amide (II).Protection of the phenolic hydroxyl of (II) with t-butyldimethylsilyl chloride leads to the silyl ether (III),which is further reacted with di-t-butyl dicarbonate in the presence of DMAP to furnish the tri-Boc derivative (IV).Subsequent desilylation of (IV) by means of tetrabutylammonium fluoride affords the tri-Boc-tyrosinamide (V).

合成路线:Tetrazole-catalyzed phosphitylation of the tyrosinamide derivative (V) with O-2-(pivaloylthio)ethyl-N,N,N',N'-tetraisopropylphosphorodiamidite (VI) yields phosphoramidite (VII).This is subsequently coupled to azidothimidine (VIII) to furnish phosphite (IX),which is then oxidized to the corresponding phosphate (X) with t-butyl hydroperoxide.The N-Boc protecting groups of (X) are finally removed under acidic conditions to provide the title compound.