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A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams
An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dicta...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8464940/ https://www.ncbi.nlm.nih.gov/pubmed/34576929 http://dx.doi.org/10.3390/molecules26185459 |
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author | Szcześniak, Piotr Grzeszczyk, Barbara Furman, Bartłomiej |
author_facet | Szcześniak, Piotr Grzeszczyk, Barbara Furman, Bartłomiej |
author_sort | Szcześniak, Piotr |
collection | PubMed |
description | An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives. |
format | Online Article Text |
id | pubmed-8464940 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-84649402021-09-27 A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams Szcześniak, Piotr Grzeszczyk, Barbara Furman, Bartłomiej Molecules Article An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives. MDPI 2021-09-08 /pmc/articles/PMC8464940/ /pubmed/34576929 http://dx.doi.org/10.3390/molecules26185459 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Szcześniak, Piotr Grzeszczyk, Barbara Furman, Bartłomiej A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title | A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title_full | A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title_fullStr | A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title_full_unstemmed | A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title_short | A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams |
title_sort | convenient approach towards the synthesis of admdp type iminosugars and nojirimycin derivatives from sugar-derived lactams |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8464940/ https://www.ncbi.nlm.nih.gov/pubmed/34576929 http://dx.doi.org/10.3390/molecules26185459 |
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