Synthesis of a sucrose dimer with enone tether; a study on its functionalization

The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double b...

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Autores principales: Pakulski, Zbigniew, Gajda, Norbert, Jawiczuk, Magdalena, Frelek, Jadwiga, Cmoch, Piotr, Jarosz, Sławomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077423/
https://www.ncbi.nlm.nih.gov/pubmed/24991275
http://dx.doi.org/10.3762/bjoc.10.124
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author Pakulski, Zbigniew
Gajda, Norbert
Jawiczuk, Magdalena
Frelek, Jadwiga
Cmoch, Piotr
Jarosz, Sławomir
author_facet Pakulski, Zbigniew
Gajda, Norbert
Jawiczuk, Magdalena
Frelek, Jadwiga
Cmoch, Piotr
Jarosz, Sławomir
author_sort Pakulski, Zbigniew
collection PubMed
description The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.
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spelling pubmed-40774232014-07-02 Synthesis of a sucrose dimer with enone tether; a study on its functionalization Pakulski, Zbigniew Gajda, Norbert Jawiczuk, Magdalena Frelek, Jadwiga Cmoch, Piotr Jarosz, Sławomir Beilstein J Org Chem Full Research Paper The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology. Beilstein-Institut 2014-05-28 /pmc/articles/PMC4077423/ /pubmed/24991275 http://dx.doi.org/10.3762/bjoc.10.124 Text en Copyright © 2014, Pakulski et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Pakulski, Zbigniew
Gajda, Norbert
Jawiczuk, Magdalena
Frelek, Jadwiga
Cmoch, Piotr
Jarosz, Sławomir
Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title_full Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title_fullStr Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title_full_unstemmed Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title_short Synthesis of a sucrose dimer with enone tether; a study on its functionalization
title_sort synthesis of a sucrose dimer with enone tether; a study on its functionalization
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077423/
https://www.ncbi.nlm.nih.gov/pubmed/24991275
http://dx.doi.org/10.3762/bjoc.10.124
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