ArticleThe Journal of organic chemistry2017
Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Hypervalent chalcogenonium organocatalysis for the direct stereoselective synthesis of deoxyglycosides from hemiacetals.Chemical science · 2026Article
- Enantioselective Route to Terminal 2,3-Epoxy Tosylates Enabled by Cooperative Organocatalytic Desymmetrization of 2-Substituted Glycerol Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Sigma hole donor XB and ChB catalysis in oligosaccharide synthesis.Trends in chemistry · 2025Article
- Article
- β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas.Journal of the American Chemical Society · 2024Article
- Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin.Organic letters · 2023Article
- Recent Advances in Stereoselective ChemicalFrontiers in molecular biosciences · 2022Review
- Exploiting non-covalent interactions in selective carbohydrate synthesis.Nature reviews. Chemistry · 2021Review
- A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling.Nature communications · 2020Article
- Mechanism and origins of selectivity in the enantioselective oxa-Pictet-Spengler reaction: a cooperative catalytic complex from a hydrogen bond donor and chiral phosphoric acid.Chemical science · 2020Article
- Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.Journal of the American Chemical Society · 2020Article
- Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.Organic letters · 2020Article
- Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors.Journal of the American Chemical Society · 2020Article
- Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(CThe Journal of organic chemistry · 2019Article
- Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.Chemical science · 2019Article
- Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.Carbohydrate research · 2019Review
- A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.Angewandte Chemie (International ed. in English) · 2018Article
- An ultra-low thiourea catalyzed strain-release glycosylation and a multicatalytic diversification strategy.Nature communications · 2018Article
- Methods for 2-Deoxyglycoside Synthesis.Chemical reviews · 2018Review
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.
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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.