合成路线:This compound can be prepared by several different ways:1) The reaction of 5-fluorouridine (I) with 2,2-dimethoxypropane (A) by means of p-toluenesulfonic acid gives 2',3'-isopropylidene-5-fluorouridine (III),which is treated with triphenylphosphite methiodide in DMF to afford 5'-deoxy-5'-iodo-2',3'-isopropylidene-5-fluorouridine (IV).The reduction of (IV) with H2 over Pd/C in methanol-triethyl-amine yields 5'-deoxy-2',3'-isopropylidene-5-fluorouridine (V),which is finally hydrolyzed with aqueous trifluoroacetic acid.2) The hydrolysis of compound (IV) with aqueous trifluoroacetic acid as before gives 5'-deoxy-5'-iodouridine (II),which is finally reduced with H2 over Pd/C as before.3) Compound (II) can also be obtained by reaction of (I) with triphenyl phosphite methiodide as before.4) It can also be prepared via reduction of the 5'-chloro intermediate with tributyltin hydride.
参考文献标题:Doxifluridine
文献作者:Castar,J.; Albonico,S.M.; Serradell,M.N.; Blancafort,P.
参考来源:Drugs Fut 1981,6(2),80
合成路线:This compound can be prepared by several different ways:1) The reaction of 5-fluorouridine (I) with 2,2-dimethoxypropane (A) by means of p-toluenesulfonic acid gives 2',3'-isopropylidene-5-fluorouridine (III),which is treated with triphenylphosphite methiodide in DMF to afford 5'-deoxy-5'-iodo-2',3'-isopropylidene-5-fluorouridine (IV).The reduction of (IV) with H2 over Pd/C in methanol-triethyl-amine yields 5'-deoxy-2',3'-isopropylidene-5-fluorouridine (V),which is finally hydrolyzed with aqueous trifluoroacetic acid.2) The hydrolysis of compound (IV) with aqueous trifluoroacetic acid as before gives 5'-deoxy-5'-iodouridine (II),which is finally reduced with H2 over Pd/C as before.3) Compound (II) can also be obtained by reaction of (I) with triphenyl phosphite methiodide as before.4) It can also be prepared via reduction of the 5'-chloro intermediate with tributyltin hydride.
参考文献标题:Fluorinated pyrimidine nucleosides.3.Synthesis and antitumor activity of a series of 5'-deoxy-5-fluoropyrimidine nucleosides
文献作者:Cook,A.F.; Holman,M.J.; Kramer,M.J.; Trown,P.W.
参考来源:J Med Chem 1979,22(11),1330-35
合成路线:The condensation of bis(trimethylsilyl)fluorouracil (I) with 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose (II) in the presence of trimethylsilyl trifluoromethanesulfonate (III) gives the fully protected compound (IV),which is finally deprotected by the usual methods.
参考文献标题:Stereospecific synthesis of the anticancer agent 5'-deoxy-5-fluorouridine (5-DFUR) and its 5'-deuterated derivatives
文献作者:D'Souza,R.; Arnold,W.; Van Koeveringe,J.A.; Kiss,J.
参考来源:Helv Chim Acta 1982,65(5),1522
合成路线:This compound can be prepared by several different ways:1) The reaction of 5-fluorouridine (I) with 2,2-dimethoxypropane (A) by means of p-toluenesulfonic acid gives 2',3'-isopropylidene-5-fluorouridine (III),which is treated with triphenylphosphite methiodide in DMF to afford 5'-deoxy-5'-iodo-2',3'-isopropylidene-5-fluorouridine (IV).The reduction of (IV) with H2 over Pd/C in methanol-triethyl-amine yields 5'-deoxy-2',3'-isopropylidene-5-fluorouridine (V),which is finally hydrolyzed with aqueous trifluoroacetic acid.2) The hydrolysis of compound (IV) with aqueous trifluoroacetic acid as before gives 5'-deoxy-5'-iodouridine (II),which is finally reduced with H2 over Pd/C as before.3) Compound (II) can also be obtained by reaction of (I) with triphenyl phosphite methiodide as before.4) It can also be prepared via reduction of the 5'-chloro intermediate with tributyltin hydride.
参考文献标题:Analogs of nucleosides.XVI.5'-Halo-2',3'-sulfites in the synthesis of 2',5'-dideoxy-5-fluorouridine and related analogs
文献作者:Beranek,J.; Hrebabecky,H.
参考来源:Coll Czech Chem Commun 1978,43(15),3268-78
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