新产品编号:514659

Chemical Name: 3'-Azido-3'-deoxythymidine 5'--[11-[[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetraazacyclotetradecane-1 pentanoate]
CAS No. 220481-73-2
项目整合开发状态: Biological Testing
项目研究机构: INSERM (Originator)
合成路线:Protection of tetraazacyclotetradecane (I) with Boc2O,followed flash chromatography,provided the tri-N-Boc derivative (II) and an unseparable mixture of three isomeric di-N-Boc macrocycles (III).Alkylation of this mixture with ethyl 5-bromovalerate gave a mixture of mono- and dialkylated compounds (IV),from which the required isomer (V) was isolated by flash chromatography.Then,condensation of tri-Boc derivative (II) and monoalkylated di-Boc derivative (V) with alpha-alpha'-dibromo-p-xylene (VI) yielded the desired unsymmetrical bis-macrocycle (VII) along with two symmetrical bis-macrocycle dimers.Subsequent hydrolysis of this mixture with NaOH in the presence of a catalytic amount of Triton B,followed by chromatographic separation,provided pure carboxylic acid (VIII).Further coupling of (VIII) with azidothymidine (IX) using benzotriazol-1-yloxy-tris(pyrrolidino) phosphonium hexafluorophosphate (PyBOP),and final acid deprotection of the Boc groups furnished the title compound.