Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations

Reactions of O-peracylated C-(1-bromo-β-d-glucopyranosyl)formamides with thioamides furnished the corresponding glucopyranosylidene-spiro-thiazolin-4-one. While O-debenzoylations under a variety of conditions resulted in decomposition, during O-deacetylations the addition of MeOH to the thiazolinone...

Descripción completa

Detalles Bibliográficos
Autores principales: Szabó, Katalin E., Kun, Sándor, Mándi, Attila, Kurtán, Tibor, Somsák, László
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151563/
https://www.ncbi.nlm.nih.gov/pubmed/29048398
http://dx.doi.org/10.3390/molecules22101760
_version_ 1783357179241168896
author Szabó, Katalin E.
Kun, Sándor
Mándi, Attila
Kurtán, Tibor
Somsák, László
author_facet Szabó, Katalin E.
Kun, Sándor
Mándi, Attila
Kurtán, Tibor
Somsák, László
author_sort Szabó, Katalin E.
collection PubMed
description Reactions of O-peracylated C-(1-bromo-β-d-glucopyranosyl)formamides with thioamides furnished the corresponding glucopyranosylidene-spiro-thiazolin-4-one. While O-debenzoylations under a variety of conditions resulted in decomposition, during O-deacetylations the addition of MeOH to the thiazolinone moiety was observed, and with EtOH and water similar adducts were isolated or detected. The structure and stereochemistry of the new compounds were established by means of NMR and electronic circular dichroism (ECD) data supported by time-dependent density functional theory ECD (TDDFT-ECD) calculations. TDDFT-ECD calculations could efficiently distinguish the proposed epimeric products having different absolute configuration in the spiro heterocyclic ring.
format Online
Article
Text
id pubmed-6151563
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61515632018-11-13 Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations Szabó, Katalin E. Kun, Sándor Mándi, Attila Kurtán, Tibor Somsák, László Molecules Article Reactions of O-peracylated C-(1-bromo-β-d-glucopyranosyl)formamides with thioamides furnished the corresponding glucopyranosylidene-spiro-thiazolin-4-one. While O-debenzoylations under a variety of conditions resulted in decomposition, during O-deacetylations the addition of MeOH to the thiazolinone moiety was observed, and with EtOH and water similar adducts were isolated or detected. The structure and stereochemistry of the new compounds were established by means of NMR and electronic circular dichroism (ECD) data supported by time-dependent density functional theory ECD (TDDFT-ECD) calculations. TDDFT-ECD calculations could efficiently distinguish the proposed epimeric products having different absolute configuration in the spiro heterocyclic ring. MDPI 2017-10-19 /pmc/articles/PMC6151563/ /pubmed/29048398 http://dx.doi.org/10.3390/molecules22101760 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Szabó, Katalin E.
Kun, Sándor
Mándi, Attila
Kurtán, Tibor
Somsák, László
Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title_full Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title_fullStr Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title_full_unstemmed Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title_short Glucopyranosylidene-Spiro-Thiazolinones: Synthetic Studies and Determination of Absolute Configuration by TDDFT-ECD Calculations
title_sort glucopyranosylidene-spiro-thiazolinones: synthetic studies and determination of absolute configuration by tddft-ecd calculations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151563/
https://www.ncbi.nlm.nih.gov/pubmed/29048398
http://dx.doi.org/10.3390/molecules22101760
work_keys_str_mv AT szabokataline glucopyranosylidenespirothiazolinonessyntheticstudiesanddeterminationofabsoluteconfigurationbytddftecdcalculations
AT kunsandor glucopyranosylidenespirothiazolinonessyntheticstudiesanddeterminationofabsoluteconfigurationbytddftecdcalculations
AT mandiattila glucopyranosylidenespirothiazolinonessyntheticstudiesanddeterminationofabsoluteconfigurationbytddftecdcalculations
AT kurtantibor glucopyranosylidenespirothiazolinonessyntheticstudiesanddeterminationofabsoluteconfigurationbytddftecdcalculations
AT somsaklaszlo glucopyranosylidenespirothiazolinonessyntheticstudiesanddeterminationofabsoluteconfigurationbytddftecdcalculations

Ejemplares similares