ArticleJournal of the American Chemical Society2018
Stereoretentive C( sp
Article in Journal of the American Chemical Society, 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 trial behind it
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
11 citing papers in PubMed, 74 citations in OpenAlex.
- Silylium-Ion-Initiated Disulfidation of Internal Alkynes With Disulfides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Visible-Light-Mediated Synthesis of AnomericMolecules (Basel, Switzerland) · 2025Article
- Utilizing Reusable Catalyst Phosphotungstic Acid for the Synthesis of Thioglycoside from Per-ACS omega · 2023Article
- Stereoselective Synthesis of 2-Deoxythiosugars from Glycals.Molecules (Basel, Switzerland) · 2022Article
- Visible-Light-Mediated Stadler-Ziegler Arylation of Thiosugars with Anilines.ACS organic & inorganic Au · 2022Article
- Organometallic AlaChem catalysis · 2021Article
- Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.RSC advances · 2021Article
- Light-Mediated Cross-Coupling of Anomeric Trifluoroborates.Organic letters · 2021Article
- Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy.Chemical science · 2020Article
- Catalytic and Photochemical Strategies to Stabilized Radicals Based on Anomeric Nucleophiles.Journal of the American Chemical Society · 2020Article
- Facile triflic acid-catalyzed α-1,2-Chemical science · 2019Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.
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.