MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals

[Image: see text] The development of effective protection strategies is essential in the synthesis of complex carbohydrates and glycomimetics. This article describes a versatile four-stage protocol for the synthesis of α- or β-aryl-C-glycosides from unprotected d-glycals using two acetal protecting...

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Autores principales: Choutka, Jan, Pohl, Radek, Parkan, Kamil
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644498/
https://www.ncbi.nlm.nih.gov/pubmed/31458930
http://dx.doi.org/10.1021/acsomega.8b00901
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author Choutka, Jan
Pohl, Radek
Parkan, Kamil
author_facet Choutka, Jan
Pohl, Radek
Parkan, Kamil
author_sort Choutka, Jan
collection PubMed
description [Image: see text] The development of effective protection strategies is essential in the synthesis of complex carbohydrates and glycomimetics. This article describes a versatile four-stage protocol for the synthesis of α- or β-aryl-C-glycosides from unprotected d-glycals using two acetal protecting groups, ethoxyethyl and methoxypropyl, which are stable under harsh basic conditions and convenient for the C-1 metalation of glycals. Their stability was investigated in subsequent cross-coupling reactions with 1-iodonaphthalene followed by oxidative/reductive transformations to naphthyl-C-glycosides.
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spelling pubmed-66444982019-08-27 MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals Choutka, Jan Pohl, Radek Parkan, Kamil ACS Omega [Image: see text] The development of effective protection strategies is essential in the synthesis of complex carbohydrates and glycomimetics. This article describes a versatile four-stage protocol for the synthesis of α- or β-aryl-C-glycosides from unprotected d-glycals using two acetal protecting groups, ethoxyethyl and methoxypropyl, which are stable under harsh basic conditions and convenient for the C-1 metalation of glycals. Their stability was investigated in subsequent cross-coupling reactions with 1-iodonaphthalene followed by oxidative/reductive transformations to naphthyl-C-glycosides. American Chemical Society 2018-07-16 /pmc/articles/PMC6644498/ /pubmed/31458930 http://dx.doi.org/10.1021/acsomega.8b00901 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Choutka, Jan
Pohl, Radek
Parkan, Kamil
MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title_full MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title_fullStr MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title_full_unstemmed MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title_short MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals
title_sort mop and ee protecting groups in synthesis of α- or β-naphthyl-c-glycosides from glycals
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644498/
https://www.ncbi.nlm.nih.gov/pubmed/31458930
http://dx.doi.org/10.1021/acsomega.8b00901
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AT pohlradek mopandeeprotectinggroupsinsynthesisofaorbnaphthylcglycosidesfromglycals
AT parkankamil mopandeeprotectinggroupsinsynthesisofaorbnaphthylcglycosidesfromglycals

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