Synthesis of N‐Glycosides by Silver‐Assisted Gold Catalysis

Abstract

AbstractThe synthesis of N‐glycosides from stable glycosyl donors in a catalytic fashion is still challenging, though they exist ubiquitously in DNA, RNA, glycoproteins, and other biological molecules. Herein, silver‐assisted gold‐catalyzed activation of alkynyl glycosyl carbonate donors is shown to be a versatile approach for the synthesis of purine and pyrimidine nucleosides, asparagine glycosides and quinolin‐2‐one N‐glycosides. Thus synthesized nucleosides were subjected to the oxidation–reduction sequence for the conversion of Ribf‐ into Araf‐ nucleosides, giving access to nucleosides that are otherwise difficult to synthesize. Furthermore, the protocol is demonstrated to be suitable for the synthesis of 2’‐modified nucleosides in a facile manner. Direct attachment of an asparagine‐containing dipeptide to the glucopyranose and subsequent extrapolation to afford the dipeptide disaccharide unit of chloroviruses is yet another facet of this endeavor.