ArticleJournal of the American Chemical Society2017
Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
29 citing papers in PubMed, 78 citations in OpenAlex.
- Catalytic Enantioselective Elimination of Cyclobutanols.Journal of the American Chemical Society · 2026Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- New Marine Actinobacteria Strain,Microorganisms · 2025Article
- Development of CPA-Catalyzed β-Selective Reductive Amination of Cardenolides for the Synthesis and Biological Evaluation of Hydrolytically Stable Analogs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Creation of a macrolide antibiotic against non-tuberculousScience advances · 2025Article
- Rh(II) and Chiral Phosphoric Acid Co-catalyzed Selective O-H Insertions for StereodivergentJournal of the American Chemical Society · 2025Article
- A Ligand-Controlled Approach Enabling Gold(I)-Catalyzed Stereoinvertive Glycosylation with Primal GlycosylJournal of the American Chemical Society · 2024Article
- Selective (α)-l-Rhamnosylation and Neuroprotective Activity Exploration of Cardiotonic Steroids.ACS medicinal chemistry letters · 2024Article
- Development of Recyclable Polystyrene-Supported Phosphonic Acid Resins for Carbohydrate Immobilization and Glycosylation.The Journal of organic chemistry · 2023Article
- A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol.Nature chemistry · 2023Article
- Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin.Organic letters · 2023Article
- Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent.Organic letters · 2022Article
- Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.Journal of the American Chemical Society · 2021Article
- Exploiting non-covalent interactions in selective carbohydrate synthesis.Nature reviews. Chemistry · 2021Review
- Site-switchable mono-O-allylation of polyols.Nature communications · 2020Article
- Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.Journal of the American Chemical Society · 2020Article
- Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Site-selective acylation of natural products with BINOL-derived phosphoric acids.ACS catalysis · 2019Article
- Asymmetric Baeyer-Villiger oxidation: classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization ofChemical science · 2019Article
- Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group.The Journal of antibiotics · 2019Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
This work describes the first example of using chiral catalysts to control site-selectivity for the glycosylations of complex polyols such as 6-deoxyerythronolide B and oleandomycin-derived macrolactones. The regiodivergent introduction of sugars at the C3, C5, and C11 positions of macrolactones was achieved by selecting appropriate chiral acids as catalysts or through introduction of stoichiometric boronic acid-based additives. BINOL-based chiral phosphoric acids (CPAs) were used to catalyze highly selective glycosylations at the C5 positions of macrolactones (up to 99:1 rr), whereas the use of SPINOL-based CPAs resulted in selectivity switch and glycosylation of the C3 alcohol (up to 91:9 rr). Additionally, the C11 position of macrolactones was selectively functionalized through traceless protection of the C3/C5 diol with boronic acids prior to glycosylation. Investigation of the reaction mechanism for the CPA-controlled glycosylations revealed the involvement of covalently linked anomeric phosphates rather than oxocarbenium ion pairs as the reactive intermediates.
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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.