AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives

[Image: see text] A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α′-linked 2-deoxy trehalose analogues via AuCl(3)-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brøn...

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Autores principales: Jeanneret, Robin, Walz, Carlo, van Meerbeek, Maarten, Coppock, Sarah, Galan, M. Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442795/
https://www.ncbi.nlm.nih.gov/pubmed/35994370
http://dx.doi.org/10.1021/acs.orglett.2c02530
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author Jeanneret, Robin
Walz, Carlo
van Meerbeek, Maarten
Coppock, Sarah
Galan, M. Carmen
author_facet Jeanneret, Robin
Walz, Carlo
van Meerbeek, Maarten
Coppock, Sarah
Galan, M. Carmen
author_sort Jeanneret, Robin
collection PubMed
description [Image: see text] A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α′-linked 2-deoxy trehalose analogues via AuCl(3)-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.
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spelling pubmed-94427952022-09-06 AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives Jeanneret, Robin Walz, Carlo van Meerbeek, Maarten Coppock, Sarah Galan, M. Carmen Org Lett [Image: see text] A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α′-linked 2-deoxy trehalose analogues via AuCl(3)-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals. American Chemical Society 2022-08-22 2022-09-02 /pmc/articles/PMC9442795/ /pubmed/35994370 http://dx.doi.org/10.1021/acs.orglett.2c02530 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Jeanneret, Robin
Walz, Carlo
van Meerbeek, Maarten
Coppock, Sarah
Galan, M. Carmen
AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title_full AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title_fullStr AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title_full_unstemmed AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title_short AuCl(3)-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives
title_sort aucl(3)-catalyzed hemiacetal activation for the stereoselective synthesis of 2-deoxy trehalose derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442795/
https://www.ncbi.nlm.nih.gov/pubmed/35994370
http://dx.doi.org/10.1021/acs.orglett.2c02530
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