Diversity-oriented synthesis of glycomimetics.
Journal
Communications chemistry
ISSN: 2399-3669
Titre abrégé: Commun Chem
Pays: England
ID NLM: 101725670
Informations de publication
Date de publication:
24 Jun 2021
24 Jun 2021
Historique:
received:
01
02
2021
accepted:
07
05
2021
entrez:
25
1
2023
pubmed:
24
6
2021
medline:
24
6
2021
Statut:
epublish
Résumé
Glycomimetics are structural mimics of naturally occurring carbohydrates and represent important therapeutic leads in several disease treatments. However, the structural and stereochemical complexity inherent to glycomimetics often challenges medicinal chemistry efforts and is incompatible with diversity-oriented synthesis approaches. Here, we describe a one-pot proline-catalyzed aldehyde α-functionalization/aldol reaction that produces an array of stereochemically well-defined glycomimetic building blocks containing fluoro, chloro, bromo, trifluoromethylthio and azodicarboxylate functional groups. Using density functional theory calculations, we demonstrate both steric and electrostatic interactions play key diastereodiscriminating roles in the dynamic kinetic resolution. The utility of this simple process for generating large and diverse libraries of glycomimetics is demonstrated in the rapid production of iminosugars, nucleoside analogues, carbasugars and carbohydrates from common intermediates.
Identifiants
pubmed: 36697548
doi: 10.1038/s42004-021-00520-3
pii: 10.1038/s42004-021-00520-3
pmc: PMC9814271
doi:
Types de publication
Journal Article
Langues
eng
Pagination
96Subventions
Organisme : Gouvernement du Canada | Natural Sciences and Engineering Research Council of Canada (Conseil de Recherches en Sciences Naturelles et en Génie du Canada)
ID : 2019-06368
Informations de copyright
© 2021. The Author(s).
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