2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone

X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzyl­idene-d-xylono-1,4-lactone with diphenyl­diazo­methane proceeded smoothly to give the title compound, C(25)H(22)O(5), with no accompanying epimerization. Unlike the analogously protected lyxono lacto...

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Autores principales: Jenkinson, Sarah F., Rule, Sebastian D., Booth, Kathrine V., Fleet, George W. J., Watkin, David J., Petursson, Sigthor
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961596/
https://www.ncbi.nlm.nih.gov/pubmed/21202537
http://dx.doi.org/10.1107/S1600536808012567
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author Jenkinson, Sarah F.
Rule, Sebastian D.
Booth, Kathrine V.
Fleet, George W. J.
Watkin, David J.
Petursson, Sigthor
author_facet Jenkinson, Sarah F.
Rule, Sebastian D.
Booth, Kathrine V.
Fleet, George W. J.
Watkin, David J.
Petursson, Sigthor
author_sort Jenkinson, Sarah F.
collection PubMed
description X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzyl­idene-d-xylono-1,4-lactone with diphenyl­diazo­methane proceeded smoothly to give the title compound, C(25)H(22)O(5), with no accompanying epimerization. Unlike the analogously protected lyxono lactone, the isomeric xylono lactone has two mol­ecules present in the asymmetric unit (Z′ = 2). The 5-ring lactones adopt envelope conformations and the 6-ring ketals adopt chair conformations.
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spelling pubmed-29615962010-12-30 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone Jenkinson, Sarah F. Rule, Sebastian D. Booth, Kathrine V. Fleet, George W. J. Watkin, David J. Petursson, Sigthor Acta Crystallogr Sect E Struct Rep Online Organic Papers X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzyl­idene-d-xylono-1,4-lactone with diphenyl­diazo­methane proceeded smoothly to give the title compound, C(25)H(22)O(5), with no accompanying epimerization. Unlike the analogously protected lyxono lactone, the isomeric xylono lactone has two mol­ecules present in the asymmetric unit (Z′ = 2). The 5-ring lactones adopt envelope conformations and the 6-ring ketals adopt chair conformations. International Union of Crystallography 2008-05-07 /pmc/articles/PMC2961596/ /pubmed/21202537 http://dx.doi.org/10.1107/S1600536808012567 Text en © Jenkinson 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
Jenkinson, Sarah F.
Rule, Sebastian D.
Booth, Kathrine V.
Fleet, George W. J.
Watkin, David J.
Petursson, Sigthor
2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title_full 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title_fullStr 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title_full_unstemmed 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title_short 2-O-Benzhydryl-3,4-(S)-O-benzyl­idene-d-xylono-1,4-lactone
title_sort 2-o-benzhydryl-3,4-(s)-o-benzyl­idene-d-xylono-1,4-lactone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961596/
https://www.ncbi.nlm.nih.gov/pubmed/21202537
http://dx.doi.org/10.1107/S1600536808012567
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