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

doi:10.11944/j.issn.1000-0518.2019.03.180200

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 Liping^a,XIA Ran^b^*()

^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

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

SUN Liping, XIA Ran. Synthesis of α-Adenine Arabinoside under Solvent-and Catalyst-Free Conditions[J]. Chinese Journal of Applied Chemistry, 2019, 36(3): 300-305.

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

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