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Exploring the Mechanism of Neighboring Group Assisted Glycosylation Reactions

https://doi.org/10.1021/ja981041m
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What this work says

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

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Unexpected phenomena in glycosylations of acceptors with L‐idose configuration
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The PMO Theory of Organic Chemistry
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Competitive formation of peracetylated α- l -arabinopyranosides and β- l -arabinopyranose 1,2-(alkyl orthoacetates) in Koenigs-Knorr condensations
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The effect of high pressure on the stereospecificity of the glycosylation reaction
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Numerical integration for polyatomic systems
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Roothaan-Hartree-Fock-Slater atomic wave functions
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Ab Initio and Experimental Studies on the Protonation of Glucose in the Gas Phase
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inferredcites →https://doi.org/10.1021/jo970677dopenalex-snapshot
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inferredcites →https://doi.org/10.1021/jo971282xopenalex-snapshot
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Haworth Memorial Lecture. Synthesis of complex oligosaccharide chains of glycoproteins
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inferredcites →https://doi.org/10.1063/1.462258openalex-snapshot
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inferredcites →https://doi.org/10.1080/07328309608005699openalex-snapshot
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inferredcites →https://doi.org/10.1080/07328309708007324openalex-snapshot
Synthesis of a Single Repeat Unit of Type VIII Group BStreptococcusCapsular Polysaccharide1
inferredcites →https://doi.org/10.1103/physreva.38.3098openalex-snapshot
Density-functional exchange-energy approximation with correct asymptotic behavior
inferredcites →https://doi.org/10.1139/p80-159openalex-snapshot
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis
inferredcites →https://doi.org/10.1139/v79-335openalex-snapshot
1,2-Orthoacetate intermediates in silver trifluoromethanesulphonate promoted Koenigs–Knorr synthesis of disaccharide glycosides
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Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5′-hydroxyls for the syntheses of novel potential anticancer agents
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Recent advances in glycosylation reactions
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Recent developments in the synthesis of glycoconjugates
inferredcites →https://doi.org/10.1351/pac199163040519openalex-snapshot
Recent advances in glycosylation reactions
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The Orthoester Glycosylation Method. Variations in the Anomeric Composition of the Product with Aglycone Basicity in the Two-Step Procedure.
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The Orthoester Glycosylation Method. Part II. Variation in the Anomeric Composition of the Product with Aglycone Basicity and Steric Accessibility.
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Studies on Koenigs-Knorr Glycosidations.

What points at this work

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

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Mild and General Protocol for Selective Deacetylation of Acetyl/Benzoyl-Protected Carbohydrates
inferred← citeshttps://doi.org/10.1021/acs.joc.4c02612openalex-snapshot
Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2- trans Stereoselectivity in Nucleophilic Substitution Reactions of Furanosyl Acetals
inferred← citeshttps://doi.org/10.1021/acs.joc.5b00338openalex-snapshot
Influence of Alkoxy Groups on Rates of Acetal Hydrolysis and Tosylate Solvolysis: Electrostatic Stabilization of Developing Oxocarbenium Ion Intermediates and Neighboring-Group Participation To Form Oxonium Ions
inferred← citeshttps://doi.org/10.1021/acs.joc.5b02203openalex-snapshot
Absence of Stereodirecting Participation by 2‑ O ‑Alkoxycarbonylmethyl Ethers in 4,6‑ O ‑Benzylidene-Directed Mannosylation
inferred← citeshttps://doi.org/10.1021/acs.joc.8b00047openalex-snapshot
2-O-N-Benzylcarbamoyl as a Protecting Group To Promote β-Selective Glycosylation and Its Applications in the Stereoselective Synthesis of Oligosaccharides
inferred← citeshttps://doi.org/10.1021/acs.jpca.7b06602openalex-snapshot
Theoretical Studies of the Glycosidation of 2-O-Substituted 5-Fluorouracil: N-Regioselective Synthesis with the Phase-Transfer-Catalysis Method
inferred← citeshttps://doi.org/10.1021/acs.oprd.8b00017openalex-snapshot
Synthetic Strategies toward SGLT2 Inhibitors
inferred← citeshttps://doi.org/10.1021/acs.orglett.0c01166openalex-snapshot
Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals
inferred← citeshttps://doi.org/10.1021/acs.orglett.2c01004openalex-snapshot
Diastereoselective Substitution Reactions of Acyclic β-Alkoxy Acetals via Electrostatically Stabilized Oxocarbenium Ion Intermediates
inferred← citeshttps://doi.org/10.1021/acs.orglett.2c03256openalex-snapshot
ZnI 2 -Mediated β-Galactosylation of C2-Ether-Type Donor
inferred← citeshttps://doi.org/10.1021/acs.orglett.9b00220openalex-snapshot
1,2-trans Glycosylation via Neighboring Group Participation of 2-O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis
inferred← citeshttps://doi.org/10.1021/acscatal.2c04208openalex-snapshot
Uniquely Enabling Mechanism for Bis-oxazoline Copper(II)-Catalyzed Azidation of Pyranosides and Furanosides
inferred← citeshttps://doi.org/10.1021/bk-2006-0932.ch011openalex-snapshot
Practical Applications of Computational Studies of the Glycosylation Reaction
inferred← citeshttps://doi.org/10.1021/bk-2012-1102.ch011openalex-snapshot
Practical Applications of Computational Studies of the Glycosylation Reaction
inferred← citeshttps://doi.org/10.1021/ci500325bopenalex-snapshot
BFMP: A Method for Discretizing and Visualizing Pyranose Conformations
inferred← citeshttps://doi.org/10.1021/cr500434xopenalex-snapshot
Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance
inferred← citeshttps://doi.org/10.1021/cr9903104openalex-snapshot
Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries
inferred← citeshttps://doi.org/10.1021/cr9903454openalex-snapshot
Stereocontrolled Glycosyl Transfer Reactions with Unprotected Glycosyl Donors
inferred← citeshttps://doi.org/10.1021/ja001194lopenalex-snapshot
The Conformational Origin of the Barrier to the Formation of Neighboring Group Assistance in Glycosylation Reactions: A Dynamical Density Functional Theory Study
inferred← citeshttps://doi.org/10.1021/ja062364iopenalex-snapshot
Synthetic Studies of Complex Immunostimulants from Quillaja saponaria: Synthesis of the Potent Clinical Immunoadjuvant QS-21Aapi
inferred← citeshttps://doi.org/10.1021/ja0767783openalex-snapshot
C-Glycosylation Reactions of Sulfur-Substituted Glycosyl Donors: Evidence against the Role of Neighboring-Group Participation
inferred← citeshttps://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
inferred← citeshttps://doi.org/10.1021/ja305104bopenalex-snapshot
Synthesis, Characterization, and Coupling Reactions of Six-Membered Cyclic P-Chiral Ammonium Phosphonite–Boranes; Reactive H-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics
inferred← citeshttps://doi.org/10.1021/ja4064316openalex-snapshot
Mechanistic Insights into the Gold(I)-Catalyzed Activation of Glycosyl ortho -Alkynylbenzoates for Glycosidation
inferred← citeshttps://doi.org/10.1021/ja907252uopenalex-snapshot
β-Directing Effect of Electron-Withdrawing Groups at O-3, O-4, and O-6 Positions and α-Directing Effect by Remote Participation of 3-O-Acyl and 6-O-Acetyl Groups of Donors in Mannopyranosylations
inferred← citeshttps://doi.org/10.1021/ja992750iopenalex-snapshot
Ricin A-Chain: Kinetic Isotope Effects and Transition State Structure with Stem-Loop RNA
inferred← citeshttps://doi.org/10.1021/jacs.0c09629openalex-snapshot
Diastereomeric Cyclopentane-Based Maltosides (CPMs) as Tools for Membrane Protein Study
inferred← citeshttps://doi.org/10.1021/jacs.3c05473openalex-snapshot
Archaeal Glycerolipids Are Recognized by C-Type Lectin Receptor Mincle
inferred← citeshttps://doi.org/10.1021/jacs.5b13015openalex-snapshot
Oxidative Deamination ofN-Acetyl Neuraminic Acid: Substituent Effects and Mechanism
inferred← citeshttps://doi.org/10.1021/jacs.5c07561openalex-snapshot
Anomeric Selectivity of Glycosylations through a Machine Learning Lens
inferred← citeshttps://doi.org/10.1021/jo0508999openalex-snapshot
Stereocontrolled Formation of β-Glucosides and Related Linkages in the Absence of Neighboring Group Participation: Influence of a trans-Fused 2,3-O-Carbonate Group
inferred← citeshttps://doi.org/10.1021/jo051374jopenalex-snapshot
Glycosyl Disulfides: Novel Glycosylating Reagents with Flexible Aglycon Alteration
inferred← citeshttps://doi.org/10.1021/jo071051iopenalex-snapshot
Remarkable β-Selectivity in the Synthesis of β-1- C -Arylglucosides: Stereoselective Reduction of Acetyl-Protected Methyl 1- C -Arylglucosides without Acetoxy-Group Participation
inferred← citeshttps://doi.org/10.1021/jo102333xopenalex-snapshot
2,3-Unsaturated Allyl Glycosides as Glycosyl Donors for Selective α-Glycosylation
inferred← citeshttps://doi.org/10.1021/jo2019174openalex-snapshot
Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity
inferred← citeshttps://doi.org/10.1021/jo202563fopenalex-snapshot
Could Diastereoselectivity in the Presence of O-2 Chiral Nonparticipating Groups Be an Indicator of Glycopyranosyl Oxacarbenium Ions in Glycosylation Reactions?
inferred← citeshttps://doi.org/10.1021/jo801462ropenalex-snapshot
Installation of Electron-Donating Protective Groups, a Strategy for Glycosylating Unreactive Thioglycosyl Acceptors using the Preactivation-Based Glycosylation Method
inferred← citeshttps://doi.org/10.1021/jo801630mopenalex-snapshot
Does Neighboring Group Participation by Non-Vicinal Esters Play a Role in Glycosylation Reactions? Effective Probes for the Detection of Bridging Intermediates
inferred← citeshttps://doi.org/10.1021/jo802468popenalex-snapshot
Palladium-Controlled β-Selective Glycosylation in the Absence of the C(2)-Ester Participatory Group
inferred← citeshttps://doi.org/10.1021/jo9002807openalex-snapshot
Selective Formation of β- O -Aryl Glycosides in the Absence of the C(2)-Ester Neighboring Group
inferred← citeshttps://doi.org/10.1021/jo901639bopenalex-snapshot
Correlations Between Nucleophilicities and Selectivities in the Substitutions of Tetrahydropyran Acetals
inferred← citeshttps://doi.org/10.1021/jo902100qopenalex-snapshot
2,6-Disubstituted Benzoates As Neighboring Groups for Enhanced Diastereoselectivity in β-Galactosylation Reactions: Synthesis of β-1,3-Linked Oligogalactosides Related to Arabinogalactan Proteins
inferred← citeshttps://doi.org/10.1021/jo990424fopenalex-snapshot
On the Role of Neighboring Group Participation and Ortho Esters in β-Xylosylation: 13C NMR Observation of a Bridging 2-Phenyl-1,3-dioxalenium Ion
inferred← citeshttps://doi.org/10.1021/jo990712bopenalex-snapshot
Acyl Transfer as a Problematic Side Reaction in Polymer-Supported Oligosaccharide Synthesis
inferred← citeshttps://doi.org/10.1021/jp052197topenalex-snapshot
Conformational Pathways of Saturated Six-Membered Rings. A Static and Dynamical Density Functional Study
inferred← citeshttps://doi.org/10.1021/ol0273452openalex-snapshot
S-Benzoxazolyl (SBox) Glycosides as Novel, Versatile Glycosyl Donors for Stereoselective 1,2-Cis Glycosylation
inferred← citeshttps://doi.org/10.1021/ol300220popenalex-snapshot
Stereoselective C-Glycosylation Reactions with Arylzinc Reagents
inferred← citeshttps://doi.org/10.1021/ol801780copenalex-snapshot
Two-Step Synthesis of the Immunogenic Bacterial Glycolipid BbGL1
inferred← citeshttps://doi.org/10.1021/ol8019956openalex-snapshot
Continuum of Mechanisms for Nucleophilic Substitutions of Cyclic Acetals
inferred← citeshttps://doi.org/10.1038/nature05813openalex-snapshot
Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines
inferred← citeshttps://doi.org/10.1039/a809774gopenalex-snapshot
Recent developments in oligosaccharide synthesis
inferred← citeshttps://doi.org/10.1039/b008734nopenalex-snapshot
Glycosyldisulfides: a new class of solution and solid phase glycosyl donors
inferred← citeshttps://doi.org/10.1039/b108421fopenalex-snapshot
Influence of preparation procedure on polymer composition: synthesis and characterisation of polymethacrylates bearing β-D-glucopyranoside and β-D-galactopyranoside residues
inferred← citeshttps://doi.org/10.1039/b414503hopenalex-snapshot
Microreactor-based reaction optimization in organic chemistry—glycosylation as a challenge
inferred← citeshttps://doi.org/10.1039/b604400jopenalex-snapshot
Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation
inferred← citeshttps://doi.org/10.1039/b916088dopenalex-snapshot
Mechanism of chemical O-glycosylation: from early studies to recent discoveries
inferred← citeshttps://doi.org/10.1039/c3ob42073fopenalex-snapshot
An unusual glycosylation product from a partially protected fucosyl donor under silver triflate activation conditions
inferred← citeshttps://doi.org/10.1039/c5sc00280jopenalex-snapshot
Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry
inferred← citeshttps://doi.org/10.1039/c7cc01783aopenalex-snapshot
Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C 6 F 5 ) 3 -catalyzed glycosylation of sterically-hindered precursors
inferred← citeshttps://doi.org/10.1039/c7ob02460fopenalex-snapshot
Chemical synthesis of culmorin metabolites and their biologic role in culmorin and acetyl-culmorin treated wheat cells
inferred← citeshttps://doi.org/10.1039/c8cs00905hopenalex-snapshot
Stereo- and regioselective glycosylation with protection-less sugar derivatives: an alluring strategy to access glycans and natural products
inferred← citeshttps://doi.org/10.1039/c9cc07194fopenalex-snapshot
2- O -Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation
inferred← citeshttps://doi.org/10.1039/d0qo00314jopenalex-snapshot
Total synthesis of tumor-associated KH-1 antigen core nonasaccharide via photo-induced glycosylation
inferred← citeshttps://doi.org/10.1039/d2ob00131dopenalex-snapshot
ROESY and 13 C NMR to distinguish between d - and l -rhamnose in the α- d -Man p -(1 → 4)-β-Rha p -(1 → 3) repeating motif
inferred← citeshttps://doi.org/10.1039/d2ra01999jopenalex-snapshot
Beyond GalNAc! Drug delivery systems comprising complex oligosaccharides for targeted use of nucleic acid therapeutics
inferred← citeshttps://doi.org/10.1039/d2sc06925copenalex-snapshot
Convergent chemoenzymatic synthesis of O -GalNAc rare cores 5, 7, 8 and their sialylated forms
inferred← citeshttps://doi.org/10.1055/a-1941-3801openalex-snapshot
Zinc Acetate Catalyzed Stereoselective 1,2-trans-Glycosylation Using Glycosyl Chlorides
inferred← citeshttps://doi.org/10.1055/s-0036-1588722openalex-snapshot
2,6-Lactones as a New Entry in Stereoselective Glycosylations
inferred← citeshttps://doi.org/10.1055/sos-sd-228-00279openalex-snapshot
13 The Controlled Synthesis of Carbohydrates
inferred← citeshttps://doi.org/10.1063/5.0289569openalex-snapshot
Semi-empirical metadynamics simulations for chemical glycosylation reactions
inferred← citeshttps://doi.org/10.1080/07328303.2010.508141openalex-snapshot
Neighboring Group Participation in Glycosylation Reactions by 2,6-Disubstituted 2- O -Benzoyl groups: A Mechanistic Investigation
inferred← citeshttps://doi.org/10.1080/07328303.2012.749264openalex-snapshot
Mechanism of Chemical Glycosylation: Focus on the Mode of Activation and Departure of Anomeric Leaving Groups
inferred← citeshttps://doi.org/10.1080/07328303.2017.1365369openalex-snapshot
Proton transfer and hydrogen bonding in glycosylation reactions
inferred← citeshttps://doi.org/10.1080/07328303.2018.1462372openalex-snapshot
Immobilization of glycans on solid surfaces for application in glycomics
inferred← citeshttps://doi.org/10.1080/07328303.2019.1630839openalex-snapshot
An extensive review of studies on mycobacterium cell wall polysaccharide-related oligosaccharides – part I: Synthetic studies on arabinofuranosyl oligosaccharides
inferred← citeshttps://doi.org/10.1080/07328303.2019.1630841openalex-snapshot
An extensive review of studies on mycobacterium cell wall polysaccharide-related oligosaccharides – part III: synthetic studies and biological applications of arabinofuranosyl oligosaccharides and their analogs, derivatives and conjugates
inferred← citeshttps://doi.org/10.1081/car-100108659openalex-snapshot
SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS. III. EFFECT OF BENZOYL GROUP AT O-3 ON STEREOSELECTIVITY OF GLYCOSYLATION BY 3-O- AND 3,4-DI-O-BENZOYLATED 2-O-BENZYLFUCOSYL BROMIDES
inferred← citeshttps://doi.org/10.1093/bbb/zbad093openalex-snapshot
Chemical synthesis of oligosaccharide derivatives with partial structure of β1-3/1-6 glucan, using monomeric units for the formation of β1-3 and β1-6 glucosidic linkages
inferred← citeshttps://doi.org/10.1134/s1068162021010258openalex-snapshot
Protecting Groups as a Factor of Stereocontrol in Glycosylation Reactions
inferred← citeshttps://doi.org/10.1134/s1068162022020108openalex-snapshot
Synthesis of Oligosaccharides Structurally Related to Hyaluronic Acid Fragments
inferred← citeshttps://doi.org/10.1139/v09-146openalex-snapshot
A facile method for the preparation of sugar orthoesters promoted by anhydrous sodium bicarbonate
inferred← citeshttps://doi.org/10.1139/v2012-056openalex-snapshot
2-(Selenocyanatomethyl)-2-propenol — A convenient synthon for ligation via the deselenative allylic rearrangement of allyl selenosulfides: preparation, functional group compatibility, and application
inferred← citeshttps://doi.org/10.1522/18261047openalex-snapshot
Formation de glycoside a partir de l'acide betulinique /
inferred← citeshttps://doi.org/10.26434/chemrxiv-2023-t45q6openalex-snapshot
Anomeric Triflates vs Dioxanium ions: Different Product-Forming Intermediates from 1-Thiophenyl-2-O-Benzyl-3-O-Benzoyl-4,6-O-Benzylidene-Mannose and Glucose
inferred← citeshttps://doi.org/10.3389/fmolb.2022.896187openalex-snapshot
Recent Advances in Stereoselective Chemical O-Glycosylation Reactions
inferred← citeshttps://doi.org/10.3390/antiox15010123openalex-snapshot
Potent Nrf2-Inducing C6-Isothiocyanate Glucose Derivatives with Dual Antioxidant and Antitumor Activity
inferred← citeshttps://doi.org/10.3390/molecules29122850openalex-snapshot
Design and Synthesis of Thiourea-Conjugating Organic Arsenic D-Glucose with Anticancer Activities
inferred← citeshttps://doi.org/10.3390/molecules31183145openalex-snapshot
The Computational Study of the Mechanism of the Acid-Promoted Pyranoside-into-Furanoside Rearrangement
inferred← citeshttps://doi.org/10.4052/tigg.23.53openalex-snapshot
Remote Participation of Protecting Groups at Remote Positions of Donors in Glycosylations
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