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

doi:10.11944/j.issn.1000-0518.2015.12.150232

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 Ran^a^*(),SUN Liping^b,YANG Xining^c,QU Guirong^d^*()

^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 Published:2015-12-01 Online:2015-12-01
Contact: XIA Ran,QU Guirong
Supported by:
Supported by the National Natural Science Foundation of China(No.21372066)

Abstract

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

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.

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

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