An efficient method for the synthesis of β-D-ribonucleosides catalyzed by metal iodides

Article abstract of DOI:10.1080/07328319608002367

Several β-D-ribonucleosides were synthesized in high yields under mild conditions by N-glycosylations of methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI₂, SbI₃ or TeI₄. A deprotection of N⁶-benzoyl group of coupling product took place to a considerable extent when N⁶-benzoyl-N⁶,N⁹-bis(trimethylsilyl)adenine was employed as a nucleoside base using SnI₂ or SnCI₂ as a catalyst while it was minimized when SbI₃ or TeI₄ was used. Further, the N-glycosylation of 1 with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile.