Influence of C-4 Axial/Equatorial Configuration and Neighboring Group/Remote Group Participation (NGP/RGP) Driven Conformational Evidence in Chemoselective …

N Kumar, A Gurawa, A Yadav, S Kashyap - Organic Letters, 2024 - ACS Publications
Organic Letters, 2024ACS Publications
We herein reveal the possibility of the C-4 neighboring group/remote group participation
(NGP/RGP) facilitating the stabilization of the anomeric center via dioxolenium intermediates
in the chemoselective activation of glycal donors. We further realized that the
axial/equatorial configuration of the C-4 group in the galacto-and gluco-glycal series
enables diverse pathways to give direct 1, 2-addition or Ferrier rearrangement, respectively.
A proof-of-principle for stereoselective glycosylation was amply illustrated by employing …
We herein reveal the possibility of the C-4 neighboring group/remote group participation (NGP/RGP) facilitating the stabilization of the anomeric center via dioxolenium intermediates in the chemoselective activation of glycal donors. We further realized that the axial/equatorial configuration of the C-4 group in the galacto- and gluco-glycal series enables diverse pathways to give direct 1,2-addition or Ferrier rearrangement, respectively. A proof-of-principle for stereoselective glycosylation was amply illustrated by employing carbohydrates, amino acids, natural products, and bioactive molecules to develop 2-deoxy-glycan analogs.
ACS Publications
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