4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside

The title compound, C(21)H(26)O(10)S, was synthesized in a single step from mannose penta­acetate. The mol­ecular structure confirms the α configuration of the anomeric thioaryl substituent. Spectroscopic and melting-point data obtained for the title compound are in disagreement with those previousl...

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Detalles Bibliográficos
Autores principales: Drouin, Ludovic, Cowley, Andrew R., Fairbanks, Antony J., Thompson, Amber L.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962034/
https://www.ncbi.nlm.nih.gov/pubmed/21203121
http://dx.doi.org/10.1107/S1600536808019338
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author Drouin, Ludovic
Cowley, Andrew R.
Fairbanks, Antony J.
Thompson, Amber L.
author_facet Drouin, Ludovic
Cowley, Andrew R.
Fairbanks, Antony J.
Thompson, Amber L.
author_sort Drouin, Ludovic
collection PubMed
description The title compound, C(21)H(26)O(10)S, was synthesized in a single step from mannose penta­acetate. The mol­ecular structure confirms the α configuration of the anomeric thioaryl substituent. Spectroscopic and melting-point data obtained for the title compound are in disagreement with those previously reported, indicating the previously reported synthesis [Durette & Shen (1980 ▶). Carbohydr. Res. 81, 261–274] to be erroneous. The crystal structure is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
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spelling pubmed-29620342010-12-30 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside Drouin, Ludovic Cowley, Andrew R. Fairbanks, Antony J. Thompson, Amber L. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(26)O(10)S, was synthesized in a single step from mannose penta­acetate. The mol­ecular structure confirms the α configuration of the anomeric thioaryl substituent. Spectroscopic and melting-point data obtained for the title compound are in disagreement with those previously reported, indicating the previously reported synthesis [Durette & Shen (1980 ▶). Carbohydr. Res. 81, 261–274] to be erroneous. The crystal structure is stabilized by weak inter­molecular C—H⋯O hydrogen bonds. International Union of Crystallography 2008-07-05 /pmc/articles/PMC2962034/ /pubmed/21203121 http://dx.doi.org/10.1107/S1600536808019338 Text en © Drouin et al. 2008 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Drouin, Ludovic
Cowley, Andrew R.
Fairbanks, Antony J.
Thompson, Amber L.
4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title_full 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title_fullStr 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title_full_unstemmed 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title_short 4-Methoxy­phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran­oside
title_sort 4-methoxy­phenyl 2,3,4,6-tetra-o-acetyl-1-thio-α-d-mannopyran­oside
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962034/
https://www.ncbi.nlm.nih.gov/pubmed/21203121
http://dx.doi.org/10.1107/S1600536808019338
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AT thompsonamberl 4methoxyphenyl2346tetraoacetyl1thioadmannopyranoside

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