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A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors

Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility with substrates having alkenes and the require...

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Autores principales: Vibhute, Amol M., Dhaka, Arun, Athiyarath, Vignesh, Sureshan, Kana M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6054025/
https://www.ncbi.nlm.nih.gov/pubmed/30090287
http://dx.doi.org/10.1039/c6sc00633g
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author Vibhute, Amol M.
Dhaka, Arun
Athiyarath, Vignesh
Sureshan, Kana M.
author_facet Vibhute, Amol M.
Dhaka, Arun
Athiyarath, Vignesh
Sureshan, Kana M.
author_sort Vibhute, Amol M.
collection PubMed
description Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility with substrates having alkenes and the requirement of a stoichiometric amount of promoters, co-promoters and extreme temperatures are some of the limitations. We have developed an efficient methodology for glycosylation via the activation of thioglycoside donors using a catalytic amount of AuCl(3) and without any co-promoter. The reaction is very fast, high-yielding and very facile at room temperature. The versatility of this method is evident from the facile glycosylation with both armed and disarmed donors and sterically demanding substrates (acceptors/donors) at ambient conditions, from the stability of the common protecting groups, and from the compatibility of alkene-containing substrates during the reaction.
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spelling pubmed-60540252018-08-08 A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors Vibhute, Amol M. Dhaka, Arun Athiyarath, Vignesh Sureshan, Kana M. Chem Sci Chemistry Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility with substrates having alkenes and the requirement of a stoichiometric amount of promoters, co-promoters and extreme temperatures are some of the limitations. We have developed an efficient methodology for glycosylation via the activation of thioglycoside donors using a catalytic amount of AuCl(3) and without any co-promoter. The reaction is very fast, high-yielding and very facile at room temperature. The versatility of this method is evident from the facile glycosylation with both armed and disarmed donors and sterically demanding substrates (acceptors/donors) at ambient conditions, from the stability of the common protecting groups, and from the compatibility of alkene-containing substrates during the reaction. Royal Society of Chemistry 2016-07-01 2016-03-08 /pmc/articles/PMC6054025/ /pubmed/30090287 http://dx.doi.org/10.1039/c6sc00633g Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Vibhute, Amol M.
Dhaka, Arun
Athiyarath, Vignesh
Sureshan, Kana M.
A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title_full A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title_fullStr A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title_full_unstemmed A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title_short A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
title_sort versatile glycosylation strategy via au(iii) catalyzed activation of thioglycoside donors
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6054025/
https://www.ncbi.nlm.nih.gov/pubmed/30090287
http://dx.doi.org/10.1039/c6sc00633g
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