• Title/Summary/Keyword: 8-Alkyl-2'(or 3')-azido(or amino)adenosine derivatives

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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;Kim, Bo-Seung;Han, Chy-Hyoung;O, Kwang-Joong;Kim, Sun-Ja;Chun, Jae-Chul;Lee, Jin-Ho;Kim, Sung-Eun;Hwang, Ki-Jun
    • Bulletin of the Korean Chemical Society
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    • v.27 no.7
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    • pp.986-990
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    • 2006
  • 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.