Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes

2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under...

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Autores principales: Witkowski, Grzegorz, Potopnyk, Mykhaylo A., Tiara, Karolina, Osuch-Kwiatkowska, Anna, Jarosz, Sławomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7436230/
https://www.ncbi.nlm.nih.gov/pubmed/32722067
http://dx.doi.org/10.3390/molecules25153357
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author Witkowski, Grzegorz
Potopnyk, Mykhaylo A.
Tiara, Karolina
Osuch-Kwiatkowska, Anna
Jarosz, Sławomir
author_facet Witkowski, Grzegorz
Potopnyk, Mykhaylo A.
Tiara, Karolina
Osuch-Kwiatkowska, Anna
Jarosz, Sławomir
author_sort Witkowski, Grzegorz
collection PubMed
description 2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.
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spelling pubmed-74362302020-08-24 Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes Witkowski, Grzegorz Potopnyk, Mykhaylo A. Tiara, Karolina Osuch-Kwiatkowska, Anna Jarosz, Sławomir Molecules Article 2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure. MDPI 2020-07-24 /pmc/articles/PMC7436230/ /pubmed/32722067 http://dx.doi.org/10.3390/molecules25153357 Text en © 2020 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
Witkowski, Grzegorz
Potopnyk, Mykhaylo A.
Tiara, Karolina
Osuch-Kwiatkowska, Anna
Jarosz, Sławomir
Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title_full Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title_fullStr Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title_full_unstemmed Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title_short Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
title_sort synthesis of highly oxygenated bicyclic carbasugars. remarkable difference in the reactivity of the d-gluco and d-xylo- derived trienes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7436230/
https://www.ncbi.nlm.nih.gov/pubmed/32722067
http://dx.doi.org/10.3390/molecules25153357
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