An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms

An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogeni...

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Autores principales: Wei, Xianhu, Ma, Yanxia, Wu, Qingping, Zhang, Jumei, Cai, Zhihe, Lu, Mianfei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331929/
https://www.ncbi.nlm.nih.gov/pubmed/26690097
http://dx.doi.org/10.3390/molecules201219789
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author Wei, Xianhu
Ma, Yanxia
Wu, Qingping
Zhang, Jumei
Cai, Zhihe
Lu, Mianfei
author_facet Wei, Xianhu
Ma, Yanxia
Wu, Qingping
Zhang, Jumei
Cai, Zhihe
Lu, Mianfei
author_sort Wei, Xianhu
collection PubMed
description An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%–94%) under appropriate conditions.
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spelling pubmed-63319292019-01-24 An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms Wei, Xianhu Ma, Yanxia Wu, Qingping Zhang, Jumei Cai, Zhihe Lu, Mianfei Molecules Article An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%–94%) under appropriate conditions. MDPI 2015-12-04 /pmc/articles/PMC6331929/ /pubmed/26690097 http://dx.doi.org/10.3390/molecules201219789 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wei, Xianhu
Ma, Yanxia
Wu, Qingping
Zhang, Jumei
Cai, Zhihe
Lu, Mianfei
An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title_full An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title_fullStr An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title_full_unstemmed An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title_short An Improved Helferich Method for the α/β-Stereoselective Synthesis of 4-Methylumbelliferyl Glycosides for the Detection of Microorganisms
title_sort improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331929/
https://www.ncbi.nlm.nih.gov/pubmed/26690097
http://dx.doi.org/10.3390/molecules201219789
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