ArticleThe Journal of organic chemistry2017
Stereoselectivity of Conformationally Restricted Glucosazide Donors.
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 23 papers.
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Who cites it
23 citing papers in PubMed, 62 citations in OpenAlex.
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- Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-The Journal of organic chemistry · 2025Article
- Approaches to stereoselective 1,1'-glycosylation.Beilstein journal of organic chemistry · 2025Review
- Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy.Nature synthesis · 2024Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
- Recent Advances in Chemical Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2023Review
- Mapping the effect of configuration and protecting group pattern on glycosyl acceptor reactivity.Chemical science · 2023Article
- Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals.The Journal of organic chemistry · 2022Article
- Synthesis of Azido-Globo H Analogs for Immunogenicity Evaluation.ACS central science · 2022Article
- Assembly of a Library of Pel-Oligosaccharides FeaturingFrontiers in chemistry · 2022Article
- Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion byAngewandte Chemie (International ed. in English) · 2021Article
- Glycosyl Sulfonates Beyond Triflates.Chemical record (New York, N.Y.) · 2021Review
- Ab Initio Molecular Dynamics Simulations of the SJournal of the American Chemical Society · 2021Article
- Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.Angewandte Chemie (International ed. in English) · 2021Article
- Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides.The Journal of organic chemistry · 2020Article
- Defining the SACS central science · 2019Article
- Are Brønsted Acids the True Promoter of Metal-Triflate-Catalyzed Glycosylations? A Mechanistic Probe into 1,2-ACS catalysis · 2019Article
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Glycosylations of 4,6-tethered glucosazide donors with a panel of model acceptors revealed the effect of acceptor nucleophilicity on the stereoselectivity of these donors. The differences in reactivity among the donors were evaluated in competitive glycosylation reactions, and their relative reactivities were found to be reflected in the stereoselectivity in glycosylations with a set of fluorinated alcohols as well as carbohydrate acceptors. We found that the 2-azido-2-deoxy moiety is more β-directing than its C-2-O-benzyl counterpart, as a consequence of increased destabilization of anomeric charge development by the electron-withdrawing azide. Additional disarming groups further decreased the α-selectivity of the studied donors, whereas substitution of the 4,6-benzylidene acetal with a 4,6-di-tert-butyl silylidene led to a slight increase in α-selectivity. The C-2-dinitropyridone group was also explored as an alternative for the nonparticipating azide group, but this protecting group significantly increased β-selectivity. All studied donors exhibited the same acceptor-dependent selectivity trend, and good α-selectivity could be obtained with the weakest acceptors and most reactive donors.
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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.