Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils

[Image: see text] A general strategy for the synthesis of 2N,4N′-disubstituted glycoluril enantiomers on a multigram scale using orthogonal protection is reported. The use of these glycolurils is demonstrated in the synthesis of enantiomerically pure bambus[6]uril macrocycles. Moreover, the deprotec...

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Autores principales: Slávik, Petr, Torrisi, Jacopo, Jurček, Pia, Sokolov, Jan, Šindelář, Vladimír
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10442914/
https://www.ncbi.nlm.nih.gov/pubmed/37505936
http://dx.doi.org/10.1021/acs.joc.3c00667
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author Slávik, Petr
Torrisi, Jacopo
Jurček, Pia
Sokolov, Jan
Šindelář, Vladimír
author_facet Slávik, Petr
Torrisi, Jacopo
Jurček, Pia
Sokolov, Jan
Šindelář, Vladimír
author_sort Slávik, Petr
collection PubMed
description [Image: see text] A general strategy for the synthesis of 2N,4N′-disubstituted glycoluril enantiomers on a multigram scale using orthogonal protection is reported. The use of these glycolurils is demonstrated in the synthesis of enantiomerically pure bambus[6]uril macrocycles. Moreover, the deprotection of (S)-1-phenylethyl substituents on the macrocycle was achieved, opening access to various chiral bambus[6]urils via post-macrocyclization modification strategy.
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spelling pubmed-104429142023-08-23 Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils Slávik, Petr Torrisi, Jacopo Jurček, Pia Sokolov, Jan Šindelář, Vladimír J Org Chem [Image: see text] A general strategy for the synthesis of 2N,4N′-disubstituted glycoluril enantiomers on a multigram scale using orthogonal protection is reported. The use of these glycolurils is demonstrated in the synthesis of enantiomerically pure bambus[6]uril macrocycles. Moreover, the deprotection of (S)-1-phenylethyl substituents on the macrocycle was achieved, opening access to various chiral bambus[6]urils via post-macrocyclization modification strategy. American Chemical Society 2023-07-28 /pmc/articles/PMC10442914/ /pubmed/37505936 http://dx.doi.org/10.1021/acs.joc.3c00667 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Slávik, Petr
Torrisi, Jacopo
Jurček, Pia
Sokolov, Jan
Šindelář, Vladimír
Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title_full Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title_fullStr Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title_full_unstemmed Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title_short Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
title_sort synthesis of enantiomerically pure bambus[6]urils utilizing orthogonal protection of glycolurils
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10442914/
https://www.ncbi.nlm.nih.gov/pubmed/37505936
http://dx.doi.org/10.1021/acs.joc.3c00667
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