The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)

The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline affords the corresponding 2,3-unsaturated amino ester, which was not previously detected (nor isolated) due to the unexpected rearrangement into its corresponding alcohol. In this work, we unveiled the mechanism of these reactions and optimiz...

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Autores principales: Rota, Paola, La Rocca, Paolo, Cirillo, Federica, Piccoli, Marco, Allevi, Pietro, Anastasia, Luigi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9048243/
https://www.ncbi.nlm.nih.gov/pubmed/35492520
http://dx.doi.org/10.1039/c9ra10215a
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author Rota, Paola
La Rocca, Paolo
Cirillo, Federica
Piccoli, Marco
Allevi, Pietro
Anastasia, Luigi
author_facet Rota, Paola
La Rocca, Paolo
Cirillo, Federica
Piccoli, Marco
Allevi, Pietro
Anastasia, Luigi
author_sort Rota, Paola
collection PubMed
description The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline affords the corresponding 2,3-unsaturated amino ester, which was not previously detected (nor isolated) due to the unexpected rearrangement into its corresponding alcohol. In this work, we unveiled the mechanism of these reactions and optimized the conditions to obtain either synthetic intermediate.
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spelling pubmed-90482432022-04-28 The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA) Rota, Paola La Rocca, Paolo Cirillo, Federica Piccoli, Marco Allevi, Pietro Anastasia, Luigi RSC Adv Chemistry The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline affords the corresponding 2,3-unsaturated amino ester, which was not previously detected (nor isolated) due to the unexpected rearrangement into its corresponding alcohol. In this work, we unveiled the mechanism of these reactions and optimized the conditions to obtain either synthetic intermediate. The Royal Society of Chemistry 2019-12-24 /pmc/articles/PMC9048243/ /pubmed/35492520 http://dx.doi.org/10.1039/c9ra10215a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Rota, Paola
La Rocca, Paolo
Cirillo, Federica
Piccoli, Marco
Allevi, Pietro
Anastasia, Luigi
The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title_full The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title_fullStr The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title_full_unstemmed The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title_short The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)
title_sort acidic hydrolysis of n-acetylneuraminic 4,5-oxazoline allows a direct functionalization of the c5 position of neu5ac2en (dana)
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9048243/
https://www.ncbi.nlm.nih.gov/pubmed/35492520
http://dx.doi.org/10.1039/c9ra10215a
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