ArticleCommunications chemistry2021
Diversity-oriented synthesis of glycomimetics.
Article in Communications chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
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Who cites it
8 citing papers in PubMed.
- Bicyclic δ-Thiolactone Glycomimetics: Stereoselective Synthesis and Discovery of Stereocontrolled Antiphage Activity.The Journal of organic chemistry · 2026Article
- Computational Pipeline for Accelerating the Design of Glycomimetics.Journal of chemical information and modeling · 2025Article
- A gram-scale synthesis of β-L-carbafucose for engineering antibody glycans.Communications chemistry · 2025Article
- Unmasking the halide effect in diastereoselective Grignard reactions applied to C4´ modified nucleoside synthesis.Nature communications · 2025Article
- A metabolic inhibitor blocks cellular fucosylation and enables production of afucosylated antibodies.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- An α-chloroaldehyde-based formal synthesis of eribulin.Nature communications · 2023Article
- Stereoselective Synthesis of Nojirimycin α-ACS omega · 2022Article
- Diversity-Oriented Synthesis: Amino Acetophenones as Building Blocks for the Synthesis of Natural Product Analogs.Pharmaceuticals (Basel, Switzerland) · 2021Review
Corrections and comments
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Authors and funding
15 authors.
Funding
Abstract
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.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.