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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 7
BKCSDE 27(7)
July 20, 2006 

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)
Beom-Tae Kim, Bo-Seung Kim, Chy-Hyoung Han, Kwang-Joong O, Sun-Ja Kim, Jae-Chul Chun, Jin-Ho Lee, Sung-Eun Kim, Ki-Jun Hwang*
Cyclic adenosine diphosphate ribose (cADPR), 8-Alkyl-2' (or 3')-azido (or amino)-2' (or 3')-deoxyadenosine
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.
986 - 990
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