Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives

A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurat...

Descripción completa

Detalles Bibliográficos
Autores principales: Tracz, Aleksandra, Malinowska, Martyna, Leśniak, Stanisław, Zawisza, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8952378/
https://www.ncbi.nlm.nih.gov/pubmed/35335129
http://dx.doi.org/10.3390/molecules27061764
_version_ 1784675599421276160
author Tracz, Aleksandra
Malinowska, Martyna
Leśniak, Stanisław
Zawisza, Anna
author_facet Tracz, Aleksandra
Malinowska, Martyna
Leśniak, Stanisław
Zawisza, Anna
author_sort Tracz, Aleksandra
collection PubMed
description A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.
format Online
Article
Text
id pubmed-8952378
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-89523782022-03-26 Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives Tracz, Aleksandra Malinowska, Martyna Leśniak, Stanisław Zawisza, Anna Molecules Article A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy. MDPI 2022-03-08 /pmc/articles/PMC8952378/ /pubmed/35335129 http://dx.doi.org/10.3390/molecules27061764 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tracz, Aleksandra
Malinowska, Martyna
Leśniak, Stanisław
Zawisza, Anna
Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title_full Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title_fullStr Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title_full_unstemmed Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title_short Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives
title_sort aziridine ring opening as regio- and stereoselective access to c-glycosyl-aminoethyl sulfide derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8952378/
https://www.ncbi.nlm.nih.gov/pubmed/35335129
http://dx.doi.org/10.3390/molecules27061764
work_keys_str_mv AT traczaleksandra aziridineringopeningasregioandstereoselectiveaccesstocglycosylaminoethylsulfidederivatives
AT malinowskamartyna aziridineringopeningasregioandstereoselectiveaccesstocglycosylaminoethylsulfidederivatives
AT lesniakstanisław aziridineringopeningasregioandstereoselectiveaccesstocglycosylaminoethylsulfidederivatives
AT zawiszaanna aziridineringopeningasregioandstereoselectiveaccesstocglycosylaminoethylsulfidederivatives

Ejemplares similares