On the anomeric preference of the isothiocyanato group
On the anomeric preference of the isothiocyanato group
This work is aimed at providing a systematic and comprehensive analysis of the anomeric effect exerted by the isothiocyanato (N C S) group taking the xylopyranose ring as a scaffold because enhanced effects have been detected in that ring-bearing halogen and pseudohalogen substituents. To this end, both α- and β-anomers of tri-O-acetoxypyranosyl-d-xylose have been prepared and thoroughly characterized. The axial preference of the isothiocyanato group reflects a dominant anomeric effect, whose origin could be determined through DFT calculations with identification of the stereoelectronic interactions as revealed by Natural Bond Orbital (NBO) analysis. In this way, this study expands the repertoire of groups biasing the conformation and reactivity of monosaccharides and related heterocycles.
14111-14125
Sosa-Gil, Concepción
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Babiano, Reyes
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Cintas, Pedro
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Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan Carlos
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22 July 2021
Sosa-Gil, Concepción
7fc3f890-2940-4ba2-8001-ffac3697dfdd
Babiano, Reyes
9302f0f4-ca45-4eeb-8bbc-42dd188846f0
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan Carlos
c4c41bb9-f9dc-41ff-bcbc-9e7adefd2b4c
Sosa-Gil, Concepción, Babiano, Reyes, Cintas, Pedro, Light, Mark and Palacios, Juan Carlos
(2021)
On the anomeric preference of the isothiocyanato group.
New Journal of Chemistry, 45 (31), .
(doi:10.1039/D1NJ00852H).
Abstract
This work is aimed at providing a systematic and comprehensive analysis of the anomeric effect exerted by the isothiocyanato (N C S) group taking the xylopyranose ring as a scaffold because enhanced effects have been detected in that ring-bearing halogen and pseudohalogen substituents. To this end, both α- and β-anomers of tri-O-acetoxypyranosyl-d-xylose have been prepared and thoroughly characterized. The axial preference of the isothiocyanato group reflects a dominant anomeric effect, whose origin could be determined through DFT calculations with identification of the stereoelectronic interactions as revealed by Natural Bond Orbital (NBO) analysis. In this way, this study expands the repertoire of groups biasing the conformation and reactivity of monosaccharides and related heterocycles.
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NJC-2021-000852R1_Final_Accepted-ms_On the anomeric preference of the isothiocyanato group
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Accepted/In Press date: 27 June 2021
e-pub ahead of print date: 22 July 2021
Published date: 22 July 2021
Additional Information:
Funding Information:
Generous support for this work was provided by the Junta de Extremadura and Fondo Europeo de Desarrollo Regional (Grants IB16167 and GR18015). We gratefully thank the Research & Technological Innovation and Supercomputing Center of Extremadura (CénitS) for allowing us the use of LUSITANIA computer resources.
Funding Information:
Generous support for this work was provided by the Junta de Extremadura and Fondo Europeo de Desarrollo Regional (Grants IB16167 and GR18015). We gratefully thank the Research & Technological Innovation and Supercomputing Center of Extremadura (C?nitS) for allowing us the use of LUSITANIA computer resources.
Publisher Copyright:
© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021.
Identifiers
Local EPrints ID: 450915
URI: http://eprints.soton.ac.uk/id/eprint/450915
ISSN: 1144-0546
PURE UUID: a26f40b9-f6ce-4f66-af23-a542adfb00c8
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Date deposited: 20 Aug 2021 16:33
Last modified: 06 Jun 2024 01:37
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Contributors
Author:
Concepción Sosa-Gil
Author:
Reyes Babiano
Author:
Pedro Cintas
Author:
Juan Carlos Palacios
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