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Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow...

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Autores principales: Orosz, János Máté, Ujj, Dóra, Kasal, Petr, Benkovics, Gábor, Bálint, Erika
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012048/
https://www.ncbi.nlm.nih.gov/pubmed/36925564
http://dx.doi.org/10.3762/bjoc.19.25
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author Orosz, János Máté
Ujj, Dóra
Kasal, Petr
Benkovics, Gábor
Bálint, Erika
author_facet Orosz, János Máté
Ujj, Dóra
Kasal, Petr
Benkovics, Gábor
Bálint, Erika
author_sort Orosz, János Máté
collection PubMed
description The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow conditions. After the optimization, the reaction steps were coupled in a semi-continuous flow system, since a solvent exchange had to be performed after the tosylation. However, the azidation and the reduction steps were compatible to be coupled in one flow system obtaining 6-monoamino-6-monodeoxy-β-cyclodextrin in a high yield. Our flow method developed is safer and faster than the batch approaches.
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spelling pubmed-100120482023-03-15 Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin Orosz, János Máté Ujj, Dóra Kasal, Petr Benkovics, Gábor Bálint, Erika Beilstein J Org Chem Full Research Paper The first continuous flow method was developed for the synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin starting from native β-cyclodextrin through three reaction steps, such as monotosylation, azidation and reduction. All reaction steps were studied separately and optimized under continuous flow conditions. After the optimization, the reaction steps were coupled in a semi-continuous flow system, since a solvent exchange had to be performed after the tosylation. However, the azidation and the reduction steps were compatible to be coupled in one flow system obtaining 6-monoamino-6-monodeoxy-β-cyclodextrin in a high yield. Our flow method developed is safer and faster than the batch approaches. Beilstein-Institut 2023-03-09 /pmc/articles/PMC10012048/ /pubmed/36925564 http://dx.doi.org/10.3762/bjoc.19.25 Text en Copyright © 2023, Orosz et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Orosz, János Máté
Ujj, Dóra
Kasal, Petr
Benkovics, Gábor
Bálint, Erika
Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title_full Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title_fullStr Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title_full_unstemmed Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title_short Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
title_sort continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012048/
https://www.ncbi.nlm.nih.gov/pubmed/36925564
http://dx.doi.org/10.3762/bjoc.19.25
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