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Synthesis of rigid p-terphenyl-linked carbohydrate mimetics
An approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described. Unnatural divalent rigid p-terphenyl-linked C-aryl glycosides with 2.0 nm dimension are available using Suzuki cross-couplings. The key compound, a p-bromophenyl-substit...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142845/ https://www.ncbi.nlm.nih.gov/pubmed/25161733 http://dx.doi.org/10.3762/bjoc.10.182 |
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author | Kandziora, Maja Reissig, Hans-Ulrich |
author_facet | Kandziora, Maja Reissig, Hans-Ulrich |
author_sort | Kandziora, Maja |
collection | PubMed |
description | An approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described. Unnatural divalent rigid p-terphenyl-linked C-aryl glycosides with 2.0 nm dimension are available using Suzuki cross-couplings. The key compound, a p-bromophenyl-substituted 1,2-oxazine, was prepared by a stereoselective [3 + 3]-cyclization of a D-isoascorbic acid-derived (Z)-nitrone and lithiated TMSE-allene. The Lewis acid-induced rearrangement of this heterocycle provided the corresponding bicyclic 1,2-oxazine derivative that may be regarded as internally protected amino sugar analogue. After subsequent reduction of the carbonyl group, the resulting bicyclic compound was used for Suzuki cross-couplings to form biphenyl aminopyran or p-terphenyl-linked dimers. Hydrogenolysis afforded new unnatural aminosugar mimetics. Zinc in the presence of acid or samarium diiodide were examined for the N–O bond cleavage in order to obtain the rigid p-terphenyl-linked C-glycosyl dimers. |
format | Online Article Text |
id | pubmed-4142845 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-41428452014-08-26 Synthesis of rigid p-terphenyl-linked carbohydrate mimetics Kandziora, Maja Reissig, Hans-Ulrich Beilstein J Org Chem Full Research Paper An approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described. Unnatural divalent rigid p-terphenyl-linked C-aryl glycosides with 2.0 nm dimension are available using Suzuki cross-couplings. The key compound, a p-bromophenyl-substituted 1,2-oxazine, was prepared by a stereoselective [3 + 3]-cyclization of a D-isoascorbic acid-derived (Z)-nitrone and lithiated TMSE-allene. The Lewis acid-induced rearrangement of this heterocycle provided the corresponding bicyclic 1,2-oxazine derivative that may be regarded as internally protected amino sugar analogue. After subsequent reduction of the carbonyl group, the resulting bicyclic compound was used for Suzuki cross-couplings to form biphenyl aminopyran or p-terphenyl-linked dimers. Hydrogenolysis afforded new unnatural aminosugar mimetics. Zinc in the presence of acid or samarium diiodide were examined for the N–O bond cleavage in order to obtain the rigid p-terphenyl-linked C-glycosyl dimers. Beilstein-Institut 2014-07-30 /pmc/articles/PMC4142845/ /pubmed/25161733 http://dx.doi.org/10.3762/bjoc.10.182 Text en Copyright © 2014, Kandziora and Reissig 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 Kandziora, Maja Reissig, Hans-Ulrich Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title | Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title_full | Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title_fullStr | Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title_full_unstemmed | Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title_short | Synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
title_sort | synthesis of rigid p-terphenyl-linked carbohydrate mimetics |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142845/ https://www.ncbi.nlm.nih.gov/pubmed/25161733 http://dx.doi.org/10.3762/bjoc.10.182 |
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