ArticleNature communications2023
Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 33 citations in OpenAlex.
- Stereoselective Ferrier-Type O-Glycosylation Enabled by Difluoromethylated Glycal Donors.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- A syntheticScience advances · 2026Article
- Enhanced Selectivity of Chalcogen Bonding over Halogen Bonding Catalyzed C-glycosylation Through Differentiated Intermediate Activation.Angewandte Chemie (International ed. in English) · 2026Article
- A universal O-glycosylation platform enabled by pyridinium catalysis using gas-releasing oxazolidinone-based carbamates donors.Nature communications · 2025Article
- Sustainable Natural Product Glycosylation: A Critical Evaluation of Biocatalytic and Chemical Approaches.ChemSusChem · 2025Review
- N-Glycosylation-The Behind-the-Scenes 'Manipulative Hand' of Plant Pathogen Invasiveness.Molecular plant pathology · 2025Review
- Dynamically Generated Carbenium Species via Photoisomerization of Cyclic Alkenes: Mild Friedel-Crafts Alkylation.The Journal of organic chemistry · 2025Article
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions.Molecules (Basel, Switzerland) · 2024Review
- Catalyst-free and wavelength-tuned glycosylation based on excited-state intramolecular proton transfer.Nature communications · 2024Article
- Zinc(ii)-mediated stereoselective construction of 1,2-Chemical science · 2024Article
- EfficientChemical science · 2024Article
- Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosylation employing glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a readily accessible and non-toxic Sc(III) catalyst system. The glycosylation reaction involves a novel activation mode of glycosyl esters driven by the ring-strain release of an intramolecularly incorporated donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables highly efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, as exemplified by the convenient preparation of the synthetically challenging chitooligosaccharide derivatives. Of note, a gram-scale synthesis of tetrasaccharide corresponding to Lipid IV with modifiable handles is achieved using the catalytic strain-release glycosylation. These attractive features promise this donor to be the prototype for developing next generation of catalytic glycosylation.
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