Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- a...

Descripción completa

Detalles Bibliográficos
Autores principales: Křenek, Karel, Šimon, Petr, Weignerová, Lenka, Fliedrová, Barbora, Kuzma, Marek, Křen, Vladimír
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326621/
https://www.ncbi.nlm.nih.gov/pubmed/22509213
http://dx.doi.org/10.3762/bjoc.8.48
_version_ 1782229538725429248
author Křenek, Karel
Šimon, Petr
Weignerová, Lenka
Fliedrová, Barbora
Kuzma, Marek
Křen, Vladimír
author_facet Křenek, Karel
Šimon, Petr
Weignerová, Lenka
Fliedrová, Barbora
Kuzma, Marek
Křen, Vladimír
author_sort Křenek, Karel
collection PubMed
description The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.
format Online
Article
Text
id pubmed-3326621
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-33266212012-04-16 Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline Křenek, Karel Šimon, Petr Weignerová, Lenka Fliedrová, Barbora Kuzma, Marek Křen, Vladimír Beilstein J Org Chem Full Research Paper The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio. Beilstein-Institut 2012-03-20 /pmc/articles/PMC3326621/ /pubmed/22509213 http://dx.doi.org/10.3762/bjoc.8.48 Text en Copyright © 2012, Křenek et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Křenek, Karel
Šimon, Petr
Weignerová, Lenka
Fliedrová, Barbora
Kuzma, Marek
Křen, Vladimír
Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title_full Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title_fullStr Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title_full_unstemmed Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title_short Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
title_sort facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-d-mannopyranosides from mannac-oxazoline
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326621/
https://www.ncbi.nlm.nih.gov/pubmed/22509213
http://dx.doi.org/10.3762/bjoc.8.48
work_keys_str_mv AT krenekkarel facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline
AT simonpetr facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline
AT weignerovalenka facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline
AT fliedrovabarbora facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline
AT kuzmamarek facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline
AT krenvladimir facilesynthesisofnitrophenyl2acetamido2deoxyadmannopyranosidesfrommannacoxazoline

Ejemplares similares