ArticleNature communications2018
Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
11 citing papers in PubMed, 45 citations in OpenAlex.
- SOrganic letters · 2025Article
- Nitrene-mediated glycosylation with thioglycoside donors under metal catalysis.Science advances · 2025Article
- Glycosyl Sulfonates Beyond Triflates.Chemical record (New York, N.Y.) · 2021Review
- Organometallic AlaChem catalysis · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- Catalytic and Photochemical Strategies to Stabilized Radicals Based on Anomeric Nucleophiles.Journal of the American Chemical Society · 2020Article
- Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.Journal of the American Chemical Society · 2020Article
- Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SJournal of the American Chemical Society · 2019Article
- Recent Developments in Stereoselective Chemical Glycosylation.Asian journal of organic chemistry · 2019Article
- Stereoretentive C( spJournal of the American Chemical Society · 2018Article
- Acyl Glycosides through Stereospecific Glycosyl Cross-Coupling: Rapid Access to C(spACS central science · 2018Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Oligosaccharides, one of the most abundant biopolymers, are involved in numerous biological processes. Although many efforts have been put in preparative carbohydrate chemistry, achieving optimal anomeric and regioselectivities remains challenging. Herein we describe an oxidative glycosylation method between anomeric stannanes and oxygen nucleophiles resulting in the formation of a C-O bond with consistently high anomeric control for glycosyl donors bearing a free C2-hydroxyl group. These reactions are promoted by hypervalent iodine reagents with catalytic or stoichiometric amounts of Cu or Zn salts. The generality of this transformation is demonstrated in 42 examples. Mechanistic studies indicate that the oxidative glycosylation is initiated by the hydroxyl-guided delivery of the hypervalent iodine and tosylate into the anomeric position, and results in excellent 1,2-trans selectivity. The unique mechanistic paradigm, high selectivities, and mild reaction conditions make this method suitable for the synthesis of oligosaccharides and for integration with other methodologies such as automated synthesis.
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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.