Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1’,2’]benzenoanthracene). The key step o...

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Autores principales: Bonaccorsi, Paola, Gioia, Maria Luisa Di, Leggio, Antonella, Minuti, Lucio, Papalia, Teresa, Siciliano, Carlo, Temperini, Andrea, Barattucci, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869296/
https://www.ncbi.nlm.nih.gov/pubmed/24367407
http://dx.doi.org/10.3762/bjoc.9.278
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author Bonaccorsi, Paola
Gioia, Maria Luisa Di
Leggio, Antonella
Minuti, Lucio
Papalia, Teresa
Siciliano, Carlo
Temperini, Andrea
Barattucci, Anna
author_facet Bonaccorsi, Paola
Gioia, Maria Luisa Di
Leggio, Antonella
Minuti, Lucio
Papalia, Teresa
Siciliano, Carlo
Temperini, Andrea
Barattucci, Anna
author_sort Bonaccorsi, Paola
collection PubMed
description A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1’,2’]benzenoanthracene). The key step of the synthesis was the cycloaddition of the azide to 2-propyn-1-yl β-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.
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spelling pubmed-38692962013-12-23 Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives Bonaccorsi, Paola Gioia, Maria Luisa Di Leggio, Antonella Minuti, Lucio Papalia, Teresa Siciliano, Carlo Temperini, Andrea Barattucci, Anna Beilstein J Org Chem Full Research Paper A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1’,2’]benzenoanthracene). The key step of the synthesis was the cycloaddition of the azide to 2-propyn-1-yl β-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized. Beilstein-Institut 2013-11-08 /pmc/articles/PMC3869296/ /pubmed/24367407 http://dx.doi.org/10.3762/bjoc.9.278 Text en Copyright © 2013, Bonaccorsi 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
Bonaccorsi, Paola
Gioia, Maria Luisa Di
Leggio, Antonella
Minuti, Lucio
Papalia, Teresa
Siciliano, Carlo
Temperini, Andrea
Barattucci, Anna
Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title_full Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title_fullStr Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title_full_unstemmed Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title_short Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
title_sort synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869296/
https://www.ncbi.nlm.nih.gov/pubmed/24367407
http://dx.doi.org/10.3762/bjoc.9.278
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