Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

An efficient methodology for the selective substitution of both terminal positions (C6 and C6’) in 1’,2,3,3’,4,4’-hexa-O-benzylsucrose with different unsaturated monosaccharide units is presented. Such a highly functionalized intermediate was cyclized under RCM conditions to afford a macrocyclic der...

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Autores principales: Tiara, Karolina, Potopnyk, Mykhaylo A, Jarosz, Sławomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870162/
https://www.ncbi.nlm.nih.gov/pubmed/29623125
http://dx.doi.org/10.3762/bjoc.14.50
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author Tiara, Karolina
Potopnyk, Mykhaylo A
Jarosz, Sławomir
author_facet Tiara, Karolina
Potopnyk, Mykhaylo A
Jarosz, Sławomir
author_sort Tiara, Karolina
collection PubMed
description An efficient methodology for the selective substitution of both terminal positions (C6 and C6’) in 1’,2,3,3’,4,4’-hexa-O-benzylsucrose with different unsaturated monosaccharide units is presented. Such a highly functionalized intermediate was cyclized under RCM conditions to afford a macrocyclic derivative containing a 31-membered ring in 26% yield.
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spelling pubmed-58701622018-04-05 Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms" Tiara, Karolina Potopnyk, Mykhaylo A Jarosz, Sławomir Beilstein J Org Chem Full Research Paper An efficient methodology for the selective substitution of both terminal positions (C6 and C6’) in 1’,2,3,3’,4,4’-hexa-O-benzylsucrose with different unsaturated monosaccharide units is presented. Such a highly functionalized intermediate was cyclized under RCM conditions to afford a macrocyclic derivative containing a 31-membered ring in 26% yield. Beilstein-Institut 2018-03-15 /pmc/articles/PMC5870162/ /pubmed/29623125 http://dx.doi.org/10.3762/bjoc.14.50 Text en Copyright © 2018, Tiara et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Tiara, Karolina
Potopnyk, Mykhaylo A
Jarosz, Sławomir
Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title_full Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title_fullStr Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title_full_unstemmed Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title_short Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
title_sort synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870162/
https://www.ncbi.nlm.nih.gov/pubmed/29623125
http://dx.doi.org/10.3762/bjoc.14.50
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AT jaroszsławomir synthesisofasucrosebasedmacrocyclewithunsymmetricalmonosaccharidesarms

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