Palladium-Catalyzed\nStereospecific Glycosylation Enables\nDivergent Synthesis of N–O-Linked Glycosides

We present a versatile palladium-catalyzed glycosylation\nplatform\nthat enables facile access to structurally diverse N–O-linked\nglycosides with constantly excellent regio- and stereoselectivities.\nImportantly, this approach offers a broad substrate scope, low catalyst\nloadings, and outstanding chemoselectivity, allowing for the selective\nreaction of oximes/hydroximic acids over hydroxyl groups that would\notherwise pose challenges in conventional glycosylation methods. The\nsynthetic utility of this method is further exemplified through a\nrange of synthetic transformations and late-stage modification of\nbioactive molecules. Overall, our method provides an efficient toolkit\nfor the synthesis of N–O-linked glycosides, which will facilitate\ntheir subsequent biological evaluations.

Publication Details

Journal
Figshare
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.orglett.4c04771.s001
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
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article

Palladium-Catalyzed\nStereospecific Glycosylation Enables\nDivergent Synthesis of N–O-Linked Glycosides

Figshare
Carbohydrate Chemistry and Synthesis
article

Palladium-Catalyzed\nStereospecific Glycosylation Enables\nDivergent Synthesis of N–O-Linked Glycosides

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Abstract

We present a versatile palladium-catalyzed glycosylation\nplatform\nthat enables facile access to structurally diverse N–O-linked\nglycosides with constantly excellent regio- and stereoselectivities.\nImportantly, this approach offers a broad substrate scope, low catalyst\nloadings, and outstanding chemoselectivity, allowing for the selective\nreaction of oximes/hydroximic acids over hydroxyl groups that would\notherwise pose challenges in conventional glycosylation methods. The\nsynthetic utility of this method is further exemplified through a\nrange of synthetic transformations and late-stage modification of\nbioactive molecules. Overall, our method provides an efficient toolkit\nfor the synthesis of N–O-linked glycosides, which will facilitate\ntheir subsequent biological evaluations.

Figshare
Openalex Percentile: Top 63%
Carbohydrate Chemistry and Synthesis
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