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Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors
Mengyu Li1, Li Song2, Liya Yang1
1Shanghai Frontiers Science Center of TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
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 one-pot saccharide synthesis, showcasing their potential for diverse synthetic applications.
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