Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (12): 1398-1401.DOI: 10.11944/j.issn.1000-0518.2015.12.150232

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Metal-free Synthesis of 2,6-Dichloropurineside and 2-Chloroadenosine

XIA Rana*(),SUN Lipingb,YANG Xiningc,QU Guirongd*()   

  1. aCollege of Chemistry and Chemical Engineering
    bSchool of Life Science and Technology,Xinxiang University,Xinxiang,He'nan 453003,China
    cXinxiang Tuoxin Biochemical Co.,Ltd.,Xinxiang,He'nan 453003,China
    dCollege of Chemistry and Chemical Engineering,He'nan Normal University,Xinxiang,He'nan 453007,China
  • Received:2015-07-06 Accepted:2015-08-27 Online:2015-12-01 Published:2015-12-01
  • Contact: XIA Ran,QU Guirong
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21372066)

Abstract:

New methods for the synthesis of 2,6-dichloropurineside and 2-chloroadenosine were developed. The key intermediate 2',3',5'-tri-O-acetyl-2,6-dichloropurineside was obtained from the condensation of 2,6-dichloropurine and β-D-ribofuranose 1,2,3,5-tetraacetate under the catalysis of 5% molar fraction of trifluoromethanesulfonic acid. 2,6-Dichloropurineside was obtained by sulfuric acid catalyzed hydrolysis of 2',3',5'-tri-O-acetyl-2,6-dichloropurineside in the yield of 89% and 2-chloroadenosine was obtained from the aminolysis of 2',3',5'-tri-O-acetyl-2,6-dichloropurineside in NH3/CH3OH with the yield of 92%. The starting substrates were all commercially available and affordable. The presented method avoided toxic metal catalysts and chromatography. Moreover, 2-thioadenosine was obtained in reliable yield on a 100 g scale.

Key words: dichloropurineside, chloroadenosine, metal-free, dichloropurine