Reagent-controlled chemo/stereoselective glycosylation of ʟ-fucal to access rare deoxysugars

Kumar, Nitin; Yadav, Monika; Kashyap, Sudhir

doi:10.1016/j.carres.2023.108992

Carbohydrate Research

2024

DOI: 10.1016/j.carres.2023.108992

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Reagent-controlled chemo/stereoselective glycosylation of ʟ-fucal to access rare deoxysugars

Nitin Kumar,

Monika Yadav,

Sudhir Kashyap

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2024

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Cited by 2 publications

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An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

Azeem,

Dubey,

Islam

et al. 2024

Chemistry An Asian Journal

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We devised a palladium‐catalyzed α‐stereoselective glycosylation that incorporates oxygen viain‐situ generation of gem‐disubstituted methanols from p‐quinone methides to access 2,3‐unsaturated gem‐diarylmethyl O‐glycosides under open‐air atmosphere at room temperature. Advantages of this environmentally friendly strategy include the absence of additives and ligands, using water as the green source of oxygen, mildest, operationally simple, exhibiting a wide functional group tolerance, and compatibility with a variety of glycal progenitors in appreciable yields. A mechanistic study has been verified via H218O labeling, which validates that water (moisture) is a sole source of oxygen.

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An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

Azeem,

Dubey,

Islam

et al. 2024

Chemistry An Asian Journal

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

Kumar,

Gurawa,

Yadav

et al. 2024

Org. Lett.

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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.

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Reagent-controlled chemo/stereoselective glycosylation of ʟ-fucal to access rare deoxysugars

Cited by 2 publications

References 126 publications

An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

An Open‐Air Palladium‐Catalyzed Stereoselective O‐Glycosylation of Glycals via in‐situ Generation of gem‐Disubstituted Methanols from p‐Quinone Methides

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

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