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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2016
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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. |
format | Online Article Text |
id | pubmed-6054025 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
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title_fullStr | A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
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title_full_unstemmed | A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
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title_short | A versatile glycosylation strategy via Au(iii) catalyzed activation of thioglycoside donors
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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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