Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry

A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as...

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Detalles Bibliográficos
Autores principales: Bozzola, Tiago, Nilsson, Ulf J., Ellervik, Ulf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016497/
https://www.ncbi.nlm.nih.gov/pubmed/35481106
http://dx.doi.org/10.1039/d2ra01576e
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author Bozzola, Tiago
Nilsson, Ulf J.
Ellervik, Ulf
author_facet Bozzola, Tiago
Nilsson, Ulf J.
Ellervik, Ulf
author_sort Bozzola, Tiago
collection PubMed
description A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as thiols and cyanide, to be used. The present investigation significantly broadens the scope of 4-aminations and allows for the introduction of a wide variety of different nucleophiles.
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spelling pubmed-90164972022-04-26 Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry Bozzola, Tiago Nilsson, Ulf J. Ellervik, Ulf RSC Adv Chemistry A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as thiols and cyanide, to be used. The present investigation significantly broadens the scope of 4-aminations and allows for the introduction of a wide variety of different nucleophiles. The Royal Society of Chemistry 2022-04-19 /pmc/articles/PMC9016497/ /pubmed/35481106 http://dx.doi.org/10.1039/d2ra01576e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Bozzola, Tiago
Nilsson, Ulf J.
Ellervik, Ulf
Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title_full Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title_fullStr Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title_full_unstemmed Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title_short Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
title_sort direct sialic acid 4-oac substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016497/
https://www.ncbi.nlm.nih.gov/pubmed/35481106
http://dx.doi.org/10.1039/d2ra01576e
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AT ellervikulf directsialicacid4oacsubstitutionbynitrogensulfurandcarbonnucleophileswithretentionofstereochemistry

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