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...

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Autores principales: Szcześniak, Piotr, Grzeszczyk, Barbara, Furman, Bartłomiej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
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.
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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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