Fiacitabine, FIAC
非西他滨Chemical Name: 1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine; 2'-Deoxy-2'-fluoro-5-iodocytarabine; 4-Amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodo-2(1H)-pyrimidinone
CAS No. 69123-90-6, 69124-05-6 (monoHCl)
项目整合开发状态: Phase II
项目研究机构: Sloan-Kettering Institute (Originator), Oclassen (Licensee)
合成路线:The reaction of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (I) with tris(trimethylsilyl)cytosine (II) in methylene chloride gives 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (III),which is hydrolyzed by treatment with methanol NH3 to afford 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (IV).Finally,this compound is iodinated by treatment with HIO3 - I2 in CCl4 - H2O - acetic acid.
📌 参考资料/链接：
参考文献标题:FIAC
文献作者:Thorpe,P.J.; Castar,J.
参考来源:Drugs Fut 1981,6(7),410
📄 详细内容
合成路线:The reaction of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (I) with tris(trimethylsilyl)cytosine (II) in methylene chloride gives 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (III),which is hydrolyzed by treatment with methanol NH3 to afford 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (IV).Finally,this compound is iodinated by treatment with HIO3 - I2 in CCl4 - H2O - acetic acid.
合成路线:FMAU is prepared by condensation of 3-O-benzoyl-2-fluoro-D-arabinosyl bromide (I) with trimethylsilylated thymine (II) followed by saponification of the protected nucleoside (III).
参考文献标题:Nucleosides.110.Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides
文献作者:Watanabe,K.A.; Reichman,U.; Hirota,K.; Lopez,C.; Fox,J.
参考来源:J Med Chem 1979,22(1),21-24
产品链接: CAS No. 69123-90-6››