Azide− Tetrazole Equilibrium of C-6 Azidopurine Nucleosides and Their Ligation Reactions with Alkynes

…, MK Singh, D Parrish, R Balachandran…

Index: Lakshman, Mahesh K.; Singh, Manish K.; Parrish, Damon; Balachandran, Raghavan; Day, Billy W. Journal of Organic Chemistry, 2010 , vol. 75, # 8 p. 2461 - 2473

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Citation Number: 51

Abstract

Facile syntheses of C-6 azidopurine ribonucleosides and 2′-deoxyribonucleosides have been developed. For silyl-and acetyl-protected as well as unprotected nucleosides, access to the azido derivatives could be readily attained via displacement of BtO− from the O 6- (benzotriazol-1-yl) inosine nucleosides by azide anion. Use of diphenylphosphoryl azide/DBU as a simple route to the acetyl-protected azido nucleosides was also evaluated ...