Beilstein J. Org. Chem.2025,21, 369–406, doi:10.3762/bjoc.21.27
, whereas protecting groups in the distal C-3, C-4, and C-6 positions are often claimed to exhibit remotegroupparticipation with the anomeric carbon. Neighbouring group participation and remotegroupparticipation are being widely studied to help the glycochemists design the synthetic protocols for
achieve better stereocontrol and to facilitate the formation of synthetically challenging glycosidic linkages.
Keywords: chemical O-glycosylation; neighbouring group participation; remotegroupparticipation; solvent effect; stereocontrol; Introduction
Cell surface glycans in living cells have
group participation (NGP)’ [70], while involvement of protecting groups in the far, distal or remote position in the glycosyl donor is often termed as ‘remotegroupparticipation’ or ‘long distance participation’ [71]. While neighbouring group participation is a much established reaction pathway, there
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Graphical Abstract
Scheme 1:
Continuum in the mechanistic pathway of glycosylation [32] reactions ranging between SN2 and SN1.