Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (3): 300-305.DOI: 10.11944/j.issn.1000-0518.2019.03.180200

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Synthesis of α-Adenine Arabinoside under Solvent-and Catalyst-Free Conditions

SUN Lipinga,XIA Ranb*()   

  1. aSchool of Life Science and Technology
    bCollege of Chemistry and Chemical Engineering,Xinxiang University,Xinxiang,He'nan 453003,China
  • Received:2018-05-29 Accepted:2018-08-29 Published:2019-03-01 Online:2019-02-28
  • Contact: XIA Ran
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21602189), the Development Project for Science and Technology of He'nan Province(No.172102310212, No.172102310213), the Key Research Projects for University of He'nan Province(No.16A150042, No.16A180035)

Abstract:

In order to develop the efficient synthesis of α-adenine arabinoside, the key intermediate 9-α-D-(2',3',5'-tri-O-acetyl)-6-chloropurineside was obtained in 85% yield from the condensation of 6-chloropurine and 1,2,3,5-tetra-O-acetatyl-β-D-arabinose under solvent- and catalyst-free conditions with microwave irradiation. α-Adenine arabinoside was synthesized from the intermediate via deacetylation catalyzed by Na2CO3, followed by aminolysis in saturated NH3/CH3OH in one pot. The intermediate was obtained in consist yield even on a 100 g scale. The analogues α-2-fluoroadenine arabinoside and α-2-aminoadenine arabinoside were obtained via similar method.

Key words: α-adenine arabinoside;, solvent-free, microwave irradiation, metal-free