Bulletin of the Korean Chemical Society

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A Convenient Synthesis of 8-Alkyl-2' (or 3')-azido (or amino)-2' (or 3')-deoxyadenosine as Diverse Synthetic Precursors of Cyclic Adenosine Diphosphate Ribose (cADPR)

  • Kim, Beom-Tae (Department of Chemistry, Chonbuk National University) ;
  • Kim, Bo-Seung (Department of Bioactive Material Sciences, College of Natural Science, Chonbuk National University) ;
  • Han, Chy-Hyoung (Department of Chemistry, Chonbuk National University) ;
  • O, Kwang-Joong (Department of Chemistry, Chonbuk National University) ;
  • Kim, Sun-Ja (Department of Chemistry, Chonbuk National University) ;
  • Chun, Jae-Chul (Division of Applied Biotechnology, College of Agriculture and Life Science, Research Center of Bioactive Materials, Chonbuk National University) ;
  • Lee, Jin-Ho (Division of Applied Biotechnology, College of Agriculture and Life Science, Research Center of Bioactive Materials, Chonbuk National University) ;
  • Kim, Sung-Eun (Division of Applied Biotechnology, College of Agriculture and Life Science, Research Center of Bioactive Materials, Chonbuk National University) ;
  • Hwang, Ki-Jun (Department of Chemistry, Chonbuk National University)
  • Published : 2006.01.20
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Abstract

As key nucleoside intermediates for the preparation of cyclic adenosine diphosphate ribose (cADPR, 1) analogues, 8-alkyl-2' (or 3')-azido(or amino)-adenosine derivatives (16-19) were successfully prepared by alkylating selectively protected adenosine derivatives (12, 13) via Pd(0) catalyzed cross-coupling reaction with tetraalkyltin reagents, followed by the sugar modification of these 8-alkyl-adenosine derivatives according to our precedent procedure. Compared to other precedent procedures, our 8-alkylation methodology using selectively TBDMS-protected 8-alkyl adenosine derivatives as starting materials will be utilized very conveniently to prepare highly functionalized adenosine analogues, which will be serve as key intermediates for the cADPR.

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References

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