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Citation: XIA Ran, SUN Liping, YANG Xining, QU Guirong. Metal-free Synthesis of 2,6-Dichloropurineside and 2-Chloroadenosine[J]. Chinese Journal of Applied Chemistry, ;2015, 32(12): 1398-1401. doi: 10.11944/j.issn.1000-0518.2015.12.150232 shu

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

XIA Ran ^a,, ,
SUN Liping ^b ,
YANG Xining ^c ,
QU Guirong ^d,,

1.
a College of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang, He'nan 453003, China;
2.
b School of Life Science and Technology, Xinxiang University, Xinxiang, He'nan 453003, China;
3.
c Xinxiang Tuoxin Biochemical Co., Ltd., Xinxiang, He'nan 453003, China;
4.
d College of Chemistry and Chemical Engineering, He'nan Normal University, Xinxiang, He'nan 453007, China

Corresponding author: XIA Ran, QU Guirong,
Received Date: 6 July 2015
Available Online: 14 August 2015
Fund Project: 国家自然科学基金(21372066)资助项目 (21372066)

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.
- dichloropurineside,
- chloroadenosine,
- metal-free,
- dichloropurine
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