-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】(-)-(3S,4S,6R,11S,11Sa)-4-Azido-11-bromo-11-methyl-3,6-epoxyperhydropyrimido[6,1-b][1,3]oxacine-8,10-dione
　　　　　　3'-Azido-5(S)-bromo-3'-deoxy-6(S)-hydroxy-5',6-anhydrothymidine

【CA登记号】224797-38-0

【分子式】C₁₀H₁₂BrN₅O₄

【分子量】346.14224

【开发单位】Universidad de Buenos Aires (Originator), Universidad Nacional de Córdoba (Originator)

【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Reverse Transcriptase Inhibitors

合成路线1

By bromination of zidovudine (AZT) (I) with N-bromosuccinimide (NBS) in DMF through the nonisolated intermediate (II), which yields a diastereomeric mixture of the target (S,S) isomer along with some (R,R) isomer that have been separated by crystallization and preparative radial chromatography.

参考文献中间体

【1】 Brinon, M.C.; Salomon, H.; Wainberg, M.; Motura, M.; Moroni, G.; Synthesis, lipophilicity and anti-HIV activity of a new brominated analog of zidovudine. Nucleosides Nucleotides 1999, 18, 3, 337.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25317	1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione	101703-35-9	C₁₀H₁₃N₅O₄	详情	详情
(II)	30897	1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-6-bromo-5-methyl-2,4-dioxopyrimidin-5-ium		C₁₀H₁₃BrN₅O₄	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)