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On the anomeric preference of the isothiocyanato group

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[double bond, length as m-dash]C[double bond, length as m-dash]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.
1144-0546
14111-14125
Sosa-Gil, Concepción
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Babiano, Reyes
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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
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, 2021 (45), 14111-14125. (doi:10.1039/D1NJ00852H).

Record type: Article

Abstract

This work is aimed at providing a systematic and comprehensive analysis of the anomeric effect exerted by the isothiocyanato (N[double bond, length as m-dash]C[double bond, length as m-dash]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.

Text
NJC-2021-000852R1_Final_Accepted-ms_On the anomeric preference of the isothiocyanato group - Accepted Manuscript
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More information

Accepted/In Press date: 27 June 2021
e-pub ahead of print date: 22 July 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
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 20 Aug 2021 16:33
Last modified: 21 Aug 2021 01:36

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Contributors

Author: Concepción Sosa-Gil
Author: Reyes Babiano
Author: Pedro Cintas
Author: Mark Light ORCID iD
Author: Juan Carlos Palacios

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