Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors

Abstract

We herein introduce glycosyl N-phenylethynyl pyrrole-2-carboxylates (PEPCs) as novel and highly efficient glycosyl donors. The unique inclusion of the pyrrole group, serving as both an electron-donating group and an ortho-tethering scaffold, imparts exceptional shelf stability while retaining reactivity for glycosylation reactions. PEPC donors exhibit broad utility for both O-and N-glycosylation across a variety of substrates. Additionally, their versatility and efficiency were further demonstrated in a onepot saccharide synthesis, showcasing their potential for diverse synthetic applications.