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Cation Clock Permits Distinction Between the Mechanisms of α- and β-O- and β-C-Glycosylation in the Mannopyranose Series: Evidence for the Existence of a Mannopyranosyl Oxocarbenium Ion

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

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A Novel Approach to the Stereoselective Synthesis of β‐Mannosides
inferredcites →https://doi.org/10.1002/anie.201100854openalex-snapshot
Indirect Cation‐Flow Method: Flash Generation of Alkoxycarbenium Ions and Studies on the Stability of Glycosyl Cations
inferredcites →https://doi.org/10.1002/chem.200701864openalex-snapshot
Automated Solid‐Phase Synthesis of Protected Oligosaccharides Containing β‐Mannosidic Linkages
inferredcites →https://doi.org/10.1002/jms.848openalex-snapshot
Anomeric distinction and oxonium ion formation in acetylated glycosides
inferredcites →https://doi.org/10.1002/jms.880openalex-snapshot
Formation and stability of oxocarbenium ions from glycosides
inferredcites →https://doi.org/10.1016/b978-0-12-386047-7.00002-3openalex-snapshot
The generation and reactions of quinone methides
inferredcites →https://doi.org/10.1016/j.crci.2010.03.016openalex-snapshot
A propos of glycosyl cations and the mechanism of chemical glycosylation
inferredcites →https://doi.org/10.1016/s0008-6215(02)00043-5openalex-snapshot
Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor?
inferredcites →https://doi.org/10.1016/s0040-4020(01)85808-7openalex-snapshot
Competition Methods and Scales for Alkyl Radical Reaction Kinetics
inferredcites →https://doi.org/10.1016/s0040-4020(01)96443-9openalex-snapshot
Regioselective manipulation of hydroxyl groups via organotin derivatives
inferredcites →https://doi.org/10.1016/s0040-4020(01)97174-1openalex-snapshot
Regio- and stereo-selectivity of alkenyl radical ring closure: A theoretical study
inferredcites →https://doi.org/10.1016/s0065-2318(09)00004-3openalex-snapshot
Chapter 4 Computational Studies of the Role of Glycopyranosyl Oxacarbenium Ions in Glycobiology and Glycochemistry
inferredcites →https://doi.org/10.1016/s0065-3160(04)39001-5openalex-snapshot
Dynamics for the reactions of ion pair intermediates of solvolysis
inferredcites →https://doi.org/10.1016/s0065-3160(06)41005-4openalex-snapshot
Mechanisms for nucleophilic aliphatic substitution at glycosides
inferredcites →https://doi.org/10.1021/ar020094copenalex-snapshot
π-Nucleophilicity in Carbon−Carbon Bond-Forming Reactions
inferredcites →https://doi.org/10.1021/ar100091mopenalex-snapshot
A Practical Guide for Estimating Rates of Heterolysis Reactions
inferredcites →https://doi.org/10.1021/ar50153a004openalex-snapshot
Free-radical clocks
inferredcites →https://doi.org/10.1021/ct1001347openalex-snapshot
Theoretical Investigation of Solvent Effects on Glycosylation Reactions: Stereoselectivity Controlled by Preferential Conformations of the Intermediate Oxacarbenium-Counterion Complex
inferredcites →https://doi.org/10.1021/ja00029a047openalex-snapshot
Stereocontrolled synthesis of disaccharides via the temporary silicon connection
inferredcites →https://doi.org/10.1021/ja00199a081openalex-snapshot
Glycosylation of unreactive substrates
inferredcites →https://doi.org/10.1021/ja00202a033openalex-snapshot
Lifetimes of oxocarbenium ions in aqueous solution from common ion inhibition of the solvolysis of .alpha.-azido ethers by added azide ion
inferredcites →https://doi.org/10.1021/ja010890yopenalex-snapshot
Reference Scales for the Characterization of Cationic Electrophiles and Neutral Nucleophiles ,
inferredcites →https://doi.org/10.1021/ja011406uopenalex-snapshot
Solid-Phase Synthesis of β-Mannosides
inferredcites →https://doi.org/10.1021/ja0122694openalex-snapshot
Stereoselective Formation of Glycosyl Sulfoxides and Their Subsequent Equilibration: Ring Inversion of an α-Xylopyranosyl Sulfoxide Dependent on the Configuration at Sulfur
inferredcites →https://doi.org/10.1021/ja0471931openalex-snapshot
Direct Chemical Synthesis of the β-Mannans: Linear and Block Syntheses of the Alternating β-(1→3)-β-(1→4)-Mannan Common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa
inferredcites →https://doi.org/10.1021/ja201249copenalex-snapshot
Hydrogen-Bonding Catalysis and Inhibition by Simple Solvents in the Stereoselective Kinetic Epoxide-Opening Spirocyclization of Glycal Epoxides to Form Spiroketals
inferredcites →https://doi.org/10.1021/ja2062715openalex-snapshot
Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst
inferredcites →https://doi.org/10.1021/ja903207bopenalex-snapshot
Can One Predict Changes from S N 1 to S N 2 Mechanisms?
inferredcites →https://doi.org/10.1021/ja971239ropenalex-snapshot
Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic Investigation
inferredcites →https://doi.org/10.1021/ja972503jopenalex-snapshot
The N-Acetyl Neuraminyl Oxecarbenium Ion Is an Intermediate in the Presence of Anionic Nucleophiles
inferredcites →https://doi.org/10.1021/jo0004106openalex-snapshot
Solvolyses of 2-Deoxy-α- and β- d -Glucopyranosyl 4‘-Bromoisoquinolinium Tetrafluoroborates
inferredcites →https://doi.org/10.1021/jo902222aopenalex-snapshot
Erosion of Stereochemical Control with Increasing Nucleophilicity: O -Glycosylation at the Diffusion Limit
inferredcites →https://doi.org/10.1021/jo9910482openalex-snapshot
Highly Diastereoselective α-Mannopyranosylation in the Absence of Participating Protecting Groups
inferredcites →https://doi.org/10.1021/jp9100448openalex-snapshot
Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Glycosylation Reactions
inferredcites →https://doi.org/10.1021/ol061938lopenalex-snapshot
1-Naphthylpropargyl Ether Group: A Readily Cleaved and Sterically Minimal Protecting System for Stereoselective Glycosylation
inferredcites →https://doi.org/10.1021/ol8017038openalex-snapshot
Is Donor−Acceptor Hydrogen Bonding Necessary for 4,6-O-Benzylidene-directed β-Mannopyranosylation? Stereoselective Synthesis of β-C-Mannopyranosides and α-C-Glucopyranosides
inferredcites →https://doi.org/10.1038/nchem.1404openalex-snapshot
Dissecting the mechanisms of a class of chemical glycosylation using primary 13C kinetic isotope effects
inferredcites →https://doi.org/10.1039/a804126aopenalex-snapshot
Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides: the exo-anomeric effect in action
inferredcites →https://doi.org/10.1039/b916088dopenalex-snapshot
Mechanism of chemical O-glycosylation: from early studies to recent discoveries
inferredcites →https://doi.org/10.1039/c004281aopenalex-snapshot
Recent advances in stereoselective glycosylation through intramolecular aglycon delivery
inferredcites →https://doi.org/10.1055/s-1988-27540openalex-snapshot
Intramolecular Addition Reactions of Allylic and Propargylic Silanes
inferredcites →https://doi.org/10.1055/s-1992-21485openalex-snapshot
Improved Synthesis of β-Mannopyranosides by Intramolecular Aglycon Delivery
inferredcites →https://doi.org/10.1055/s-2001-10798openalex-snapshot
2,4,6-Tri-tert-butylpyrimidine (TTBP): A Cost Effective, Readily Available Alternative to the Hindered Base 2,6-Di-tert-butylpyridine and its 4-Substituted Derivatives in Glycosylation and Other Reactions

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Carbocations
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STEREOCONTROLLED SYNTHESIS OF SIALOSIDES
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Stereoselective Glycosylations – Additions to Oxocarbenium Ions
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Glycosylation with Glycosyl Sulfonates
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Protecting Group Strategies in Carbohydrate Chemistry
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Synthesis of Bradyrhizose Oligosaccharides Relevant to the Bradyrhizobium O‐Antigen
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Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
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Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by 1H and 13C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters
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Synthesis of Bradyrhizose Oligosaccharides Relevant to the Bradyrhizobium O‐Antigen
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Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
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Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by 1H and 13C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters
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Mixed‐Electrolyte‐Driven Stereoselective Electrochemical Glycosylation
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Investigations of Scope and Mechanism of Nickel‐Catalyzed Transformations of Glycosyl Trichloroacetimidates to Glycosyl Trichloroacetamides and Subsequent, Atom‐Economical, One‐Step Conversion to α‐Urea‐Glycosides
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Highly Stereoselective β‐Mannopyranosylation via the 1‐α‐Glycosyloxy‐isochromenylium‐4‐gold(I) Intermediates
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Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis
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Determination of the Influence of Side‐Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors
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Statistical Analysis of Glycosylation Reactions
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Single‐Step Glycosylations with 13 C‐Labelled Sulfoxide Donors: A Low‐Temperature NMR Cartography of the Distinguishing Mechanistic Intermediates
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How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?
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Stereoselective β‐Mannosylation via Anomeric O‐Alkylation with L‐Sugar‐Derived Electrophiles
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Recent Advances in Stereocontrolled Mannosylation: Focus on Glycans Comprising Acidic and/or Amino Sugars
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Glycosylation
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Glycosylation
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Glycosyl Sulfoxides in Glycosylation Reactions
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6.01 Synthesis of Glycosides
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Stereoelectronic Effects in Glycosylation Reactions
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The Oxocarbenium Ion Intermediate
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Glycosidic bond formation methodology: challenges and impact in oligosaccharide synthesis
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In a glycosylation reaction how does a hydroxylic nucleophile find the activated anomeric carbon?
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A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art
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Contact ion pairs and solvent-separated ion pairs from d-mannopyranosyl and d-glucopyranosyl triflates
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Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal
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Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile
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Bimodal concentration-dependent reactivity pattern of a glycosyl donor: Is the solution structure involved?
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Synthesis of sialyl halides with various acyl protective groups
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Role of ion pairs in model glycosylation reactions of permethylated glucosyl and xylosyl triflates
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Unraveling chemical glycosylation: DFT insights into factors imparting stereoselectivity
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Recent advances in direct synthesis of 2-deoxy glycosides and thioglycosides
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Recent topics in β-stereoselective mannosylation
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Glycosyl Oxocarbenium Ions: Structure, Conformation, Reactivity, and Interactions
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Recent Advances in the Chemical Synthesis of C -Glycosides
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Methods for 2-Deoxyglycoside Synthesis
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Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges
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The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface
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Exploiting the Strained Ion-Pair Interactions of Sterically Hindered Pyridinium Salts Toward SN2 Glycosylation of Glycosyl Trichloroacetimidates
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Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors
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Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method
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Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A
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Absence of Stereodirecting Participation by 2‑ O ‑Alkoxycarbonylmethyl Ethers in 4,6‑ O ‑Benzylidene-Directed Mannosylation
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Stereoselectivity of Conformationally Restricted Glucosazide Donors
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Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry
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Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor
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HF-Induced Intramolecular C-Arylation and C-Alkylation/Fluorination of 2-Aminoglycopyranoses
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Blue Light Photocatalytic Glycosylation without Electrophilic Additives
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Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance
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Probing the Influence of a 4,6-O-Acetal on the Reactivity of Galactopyranosyl Donors: Verification of the Disarming Influence of thetrans–gaucheConformation of C5–C6 Bonds
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Mechanistic Insights into the Gold(I)-Catalyzed Activation of Glycosyl ortho -Alkynylbenzoates for Glycosidation
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Probing the Influence of Protecting Groups on the Anomeric Equilibrium in Sialic Acid Glycosides with the Persistent Radical Effect
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Dissecting the Essential Role of Anomeric β-Triflates in Glycosylation Reactions
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En Route to the Transformation of Glycoscience: A Chemist’s Perspective on Internal and External Crossroads in Glycochemistry
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Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR
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Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors
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Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions
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Elucidating the Curtin–Hammett Principle in Glycosylation Reactions: The Decisive Role of Equatorial Glycosyl Triflates
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Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates
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β-Stereoselective Mannosylation Using 2,6-Lactones
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An Empirical Understanding of the Glycosylation Reaction
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Impact of Aromatic Stacking on Glycoside Reactivity: Balancing CH/π and Cation/π Interactions for the Stabilization of Glycosyl-Oxocarbenium Ions
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Stereoselective C-Glycoside Formation with 2-O-Benzyl-4,6-O-benzylidene Protected 3-Deoxy Gluco- and Mannopyranoside Donors: Comparison with O-Glycoside Formation
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Influence of O6 in Mannosylations Using Benzylidene Protected Donors: Stereoelectronic or Conformational Effects?
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Theoretical Foundation for the Presence of Oxacarbenium Ions in Chemical Glycoside Synthesis
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Reagent Controlled β-Specific Dehydrative Glycosylation Reactions with 2-Deoxy-Sugars
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β-Selective Mannosylation with a 4,6-Silylene-Tethered Thiomannosyl Donor
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Catching elusive glycosyl cations in a condensed phase with HF/SbF5 superacid
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Elucidating reactive sugar-intermediates by mass spectrometry
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Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy
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Design of chemical glycosyl donors: does changing ring conformation influence selectivity/reactivity?
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Realizing the promise of chemical glycobiology
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β-Mannosylation with 4,6-benzylidene protected mannosyl donors without preactivation
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Bent bonds (τ) and the antiperiplanar hypothesis, and the reactivity at the anomeric center in pyranosides
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The influence of acceptor nucleophilicity on the glycosylation reaction mechanism
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Acceptor reactivity in glycosylation reactions
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A versatile approach to the synthesis of mannosamine glycosides
inferred← citeshttps://doi.org/10.1039/d0ob02373fopenalex-snapshot
Computational evidence of glycosyl cations
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A versatile approach to the synthesis of glycans containing mannuronic acid residues
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Stereoselective access to 2-deoxy-2-trifluoromethyl sugar mimetics by trifluoromethyl-directed 1,2- trans glycosylation
inferred← citeshttps://doi.org/10.1039/d4cc02838dopenalex-snapshot
Glycosylation with sulfoxide-based glycosyl donors
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In silicomodelling of the function of disease-related CAZymes
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2,6-Lactones as a New Entry in Stereoselective Glycosylations
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Stereochemical Aspects of the C-Glycosylation of Pyranosides and Furanosides
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Semi-empirical metadynamics simulations for chemical glycosylation reactions
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Mechanism of Chemical Glycosylation: Focus on the Mode of Activation and Departure of Anomeric Leaving Groups
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Immobilization of glycans on solid surfaces for application in glycomics
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Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction
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Recent Advances in Stereoselective Chemical O-Glycosylation Reactions
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The effect of neighbouring group participation and possible long range remote group participation in O- glycosylation
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Recent Progress of Chemical Glycosylations and Oligosaccharide Synthesis
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