ArticleAngewandte Chemie (International ed. in English)2014
A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Charting the Future of Stereoselective Carbohydrate Synthesis: The Essential Role of Cross-Disciplinary Innovation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Stereoselective Ferrier-Type O-Glycosylation Enabled by Difluoromethylated Glycal Donors.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- Article
- Synthesis of 2-Deoxyglycosides with Exclusive β-Configuration Using 2-SAc Glycosyl Bromide Donors.Molecules (Basel, Switzerland) · 2025Article
- Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides.Journal of the American Chemical Society · 2024Article
- Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Iridium-promoted deoxyglycoside synthesis: stereoselectivity and mechanistic insight.Chemical science · 2020Article
- Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.Organic letters · 2020Article
- Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration.Frontiers in chemistry · 2020Article
- Oligosaccharide Synthesis and Translational Innovation.Journal of the American Chemical Society · 2019Review
- 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
- An ultra-low thiourea catalyzed strain-release glycosylation and a multicatalytic diversification strategy.Nature communications · 2018Article
- Methods for 2-Deoxyglycoside Synthesis.Chemical reviews · 2018Review
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
- Reagent-Controlled Synthesis of the Branched Trisaccharide Fragment of the Antibiotic Saccharomicin B.Organic letters · 2018Article
- Convergent Synthesis of Sialyl LewisThe Journal of organic chemistry · 2018Article
- Synthesis of Conformationally-Locked cis- and trans-Bicyclo[4.4.0] Mono-, Di-, and Trioxadecane Modifications of Galacto- and Glucopyranose; Experimental LimitingThe Journal of organic chemistry · 2018Article
- Synthesis of LewisCarbohydrate research · 2017Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97%) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH⋅H2O (1 mol%) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
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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.