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
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.123.Synthesis of sntiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-beta-D-arabinofuranosyl)cytosines and -uracils.Some structure-activity relationships
文献作者:Watanabe,K.A.; Su,T.L.; Klein,R.S.; Chu,C.K.; Matsuda,A.; Chun,M.W.; Lopez,C.; Fox,J.J.
参考来源:J Med Chem 1983,28(2),152-156
合成路线:The reaction of 1,3,5-tri-O-benzoyl-2-O-(trifluoromethanesulfonyl)-alpha-D-ribofuranose (I) with labeled tetrabutylammonium fluoride in acetonitrile gives 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose (II),which is treated with HBr/HOAc in dichloroethane to yield 3,5-di-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide (III).The condensation of (III) with thymine bis trimethylsilyl ether (IV) in dichloroethane affords a mixture of protected nucleoside alpha and beta anomers (V) and (VI),which,without separation,is deprotected with NaOMe in methanol and submitted to HPLC chromatographic separation to provide the target unprotected and labeled beta anomer.
参考文献标题:Synthesis of [18F]-labeled 2'-deoxy-2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil ([18F]-FMAU)
文献作者:Alauddin,M.M.; et al.
参考来源:J Label Compd Radiopharm 2002,45(7),583
产品链接: CAS No. 69256-17-3››