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)

摘要

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.