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2,3-Anhydro Sugars in Glycoside Bond Synthesis. Highly Stereoselective Syntheses of Oligosaccharides Containing α- and β-Arabinofuranosyl Linkages

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What this work says

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

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Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological Consequence

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Enantioselective Synthesis with Lithium/(−)‐Sparteine Carbanion Pairs

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An improved synthesis of methyl 2,3-anhydro-α-d-lyxofuranoside

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N.m.r. spectral study of α- and β-l-arabinofuranosides

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Enantioselective desymmetrisation of achiral epoxides

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Synthesis of arabinofuranosides via low-temperature activation of thioglycosides

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Thioglycosides as Glycosyl Donors in Oligosaccharide Synthesis

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Anomeric-Oxygen Activation for Glycoside Synthesis: The Trichloroacetimidate Method

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Oxirane Derivatives of Aldoses

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Synthesis and comparative evaluation of two antiviral agents: β-l-Fd4C and β-d-Fd4C

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Regioselective, Diastereoselective, and Enantioselective Lithiation−Substitution Sequences: Reaction Pathways and Synthetic Applications

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Asymmetric Catalysis of Epoxide Ring-Opening Reactions

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AIDS-driven nucleoside chemistry.

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Recent progress in O-glycosylation methods and its application to natural products synthesis

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Glycobiology: Toward Understanding the Function of Sugars

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Polymer-supported alkyl azodicarboxylates for Mitsunobu reactions

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Glycosylation of unreactive substrates

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Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method

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1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride: A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic Linkages

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Generalizing Glycosylation: Synthesis of the Blood Group Antigens Lea, Leb, and Lex Using a Standard Set of Reaction Conditions

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Sulfenate Intermediates in the Sulfoxide Glycosylation Reaction

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Programmable One-Pot Oligosaccharide Synthesis

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Scavenging Byproducts in the Sulfoxide Glycosylation Reaction: Application to the Synthesis of Ciclamycin 0

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Arabinofuranosyl Oligosaccharides from Mycobacteria: Synthesis and Effect of Glycosylation on Ring Conformation and Hydroxymethyl Group Rotamer Populations

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Analogs of 5'-deoxy-5'-(methylthio)adenosine

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Sensitivity of 1JC1-H1 Magnitudes to Anomeric Stereochemistry in 2,3-Anhydro-O-furanosides

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Arabinofuranosides from Mycobacteria: Synthesis of a Highly Branched Hexasaccharide and Related Fragments Containing β-Arabinofuranosyl Residues

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Formation of β-Mannopyranosides of Primary Alcohols Using the Sulfoxide Method

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Direct Synthesis of β-Mannopyranosides by the Sulfoxide Method

inferredcites →https://doi.org/10.1021/jo9815406openalex-snapshot

Conversion of Pyranose Glycals to Furanose Derivatives: A New Route to Oligofuranosides

inferredcites →https://doi.org/10.1021/jo981553jopenalex-snapshot

Asymmetric Syntheses of N-Boc 2-Substituted Pyrrolidines and Piperidines by Intramolecular Cyclization

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Stereoselective Synthesis of 2-S-Phenyl-2-deoxy-β-glycosides Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycoside Donors via 1,2-Migration and Concurrent Glycosidation

inferredcites →https://doi.org/10.1021/ol006948fopenalex-snapshot

First Direct Deprotonation−Electrophile Trapping of Simple Epoxides: Synthesis of α,β-Epoxysilanes from Terminal Epoxides

inferredcites →https://doi.org/10.1021/ol007008yopenalex-snapshot

Stereocontrolled Synthesis of 2,3-Anhydro-β- d -lyxofuranosyl Glycosides

inferredcites →https://doi.org/10.1021/ol026230vopenalex-snapshot

First Asymmetric Total Synthesis of (+)-Sparteine

inferredcites →https://doi.org/10.1039/a705275hopenalex-snapshot

Tuning glycoside reactivity: New tool for efficient oligosaccharide synthesis

inferredcites →https://doi.org/10.1039/a809774gopenalex-snapshot

Recent developments in oligosaccharide synthesis

inferredcites →https://doi.org/10.1039/b005474gopenalex-snapshot

Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

inferredcites →https://doi.org/10.1039/b105369hopenalex-snapshot

Functionalised bicyclic alcohols by enantioselective α-deprotonation–rearrangement of meso-epoxides†

inferredcites →https://doi.org/10.1055/s-1998-5741openalex-snapshot

Enantioselective Nucleophilic Opening of meso Epoxides by Organolithium Reagents

inferredcites →https://doi.org/10.1134/s0006297909110170openalex-snapshot

Glycoscience. Chemistry and chemical biology

What points at this work

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

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Total Synthesis of the Hexasaccharide Arabinan Domain of Mycobacterial Arabinogalactan

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Glycosylation with Sulfoxides and Sulfinates as Donors or Promoters

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Silver( I ) trifluoromethanesulfonate (triflate)

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Silver( I ) trifluoromethanesulfonate (triflate)

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SYNTHESIS OF BACTERIAL CELL ENVELOPE COMPONENTS

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General Aspects of the Glycosidic Bond Formation

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Glycoside Synthesis from 1‐Sulfur/Selenium‐Substituted Derivatives: Sections 4.1 and 4.2

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Selective Glycosylations with Furanosides

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Protecting Group Strategies Toward Glycofuranoses

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Intrinsic Issues in the Assembly of 1,2‐Linked Oligosaccharides

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Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery

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Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery

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Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis

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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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2,3‐Anhydro Sugars in Glycoside Bond Synthesis. Highly Stereoselective Syntheses of Oligosaccharides Containing α‐ and β‐Arabinofuranosyl Linkages.

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Practical Approach for the Stereoselective Introduction of β‐Arabinofuranosides.

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Two Straightforward Strategies for the Synthesis of Thiodisaccharides with a Furanose Unit as the Nonreducing End

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A Straightforward and General Strategy Towards 1,5‐Dithio‐1‐enopyranosides

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1‐exo‐Alkylidene‐2,3‐anhydrofuranoses: Valuable Synthons in the Preparation of Furanose‐Based Templates

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Pre‐Activation‐Based Stereoselective Glycosylations

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Anhydrosugars

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Synthesis of hexasaccharide fragment of lipoarabonomannan from Mycobacteria: advantages of the benzyl-free approach

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Recent progress on the synthesis of 2-deoxy glycosides

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Glycosyl Sulfoxides in Glycosylation Reactions

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6.01 Synthesis of Glycosides

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1,2-cis O-Glycosylation Methods

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Glycosylation With Furanosides

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An efficient route to thioglycosides with the 2,3-anhydro-d-ribo stereochemistry

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Synthesis of α-d-Galf-(1→2)-d-galactitol and α-d-Galf-(1→2)[β-d-Galf-(1→3)]-d-galactitol, oligosaccharide derivatives from Bacteroides cellulosolvens glycoproteins

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Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers

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Rapid synthesis of linear homologous oligoarabinofuranosides related to mycobacterial lipoarabinomannan and a neoglycoconjugate thereof

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β-L-Arabinofuranosylation Conducted by 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl Trichloroacetimidate

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Total synthesis of the hexasaccharide arabinan domain of mycobacterial arabinogalactan

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Towards the synthesis of a 2-deoxy-2-fluoro-d-mannose building block and characterisation of an unusual 2-S-phenyl anomeric pyridinium triflate salt via 1 → 2 S-migration

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Synthesis and conformational analysis of arabinofuranosides, galactofuranosides and fructofuranosides

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Arabinosylation Modulates the Growth-Regulating Activity of the Peptide Hormone CLE40a from Soybean

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Chemical synthesis of oligosaccharides and their application in new drug research

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General chemical synthesis of cyanidin-3-O-glycosides: configuration determination and structure-activity relationship analysis

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2,3-Anhydrosugars in glycoside bond synthesis. Application to the preparation of C-2 functionalized α-d-arabinofuranosides

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2,3-Anhydrosugars in glycoside bond synthesis: application to furanosyl azides and C-glycosides

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Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

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Syntheses of novel acarviosin analogs with anhydro or unsaturated sugar moieties

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Glycosylations with 2,3-aziridinofuranose derivatives

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Diphenoxytriphenylphosphorane: A potent carbohydrate cyclodehydration reagent

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Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

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Synthesis of partially benzylated arabinofuranosides, NMR analysis, and application to oligosaccharide synthesis

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Twenty Years of Mycobacterial Glycans: Furanosides and Beyond

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The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates

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A Siloxane-Bridged Glycosyl Donor Enables Highly Stereoselective β-Xylulofuranosylation

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Conformationally Constrained Glycosyl Donors as Tools to Control Glycosylation Outcomes

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Influence of Steric Crowding on Diastereoselective Arabinofuranosylations

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Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

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Phthalic Anhydride-Mediated Direct Glycosylation of Anomeric Hydroxy Arabinofuranose: Synthesis of Repeating Oligoarabinofuranoside and Tetradecasaccharide Arabinan Motif of Mycobacterial Cell Wall

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Stereocontrolled Synthesis of α-Xylofuranosides Using a Conformationally Restricted Donor

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Mechanisms of Glycosylation Reactions Studied by Low-Temperature Nuclear Magnetic Resonance

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2,3-Anhydrosugars in Glycoside Bond Synthesis. NMR and Computational Investigations into the Mechanism of Glycosylations with 2,3-Anhydrofuranosyl Glycosyl Sulfoxides

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Practical Approach for the Stereoselective Introduction of β-Arabinofuranosides

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Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan: A Model System for Oligofuranoside−Protein Recognition

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Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor

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2,3-Anhydrosugars in Glycoside Bond Synthesis: Mechanism of 2-Deoxy-2-thioaryl Glycoside Formation

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Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors

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Stereoselective 1,2-cis Furanosylations Catalyzed by Phenanthroline

inferred← citeshttps://doi.org/10.1021/jacs.2c13641openalex-snapshot

Supramolecular Capsule-Catalyzed Highly β-Selective Furanosylation Independent of the SN1/SN2 Reaction Pathway

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Antiviral Activity of Various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-Fluoro-2′,3′-didehydro-2′,3′-dideoxyribose Pyrimidine Nucleoside Analogues against Duck Hepatitis B Virus (DHBV) and Human Hepatitis B Virus (HBV)…

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Synthesis of the Branched-Chain Sugar Aceric Acid: A Unique Component of the Pectic Polysaccharide Rhamnogalacturonan-II

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On the Use of 3,5- O -Benzylidene and 3,5- O -(Di- tert -butylsilylene)-2- O -benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method

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2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to α- d -Galactofuranosides

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inferred← citeshttps://doi.org/10.1021/jo8012397openalex-snapshot

Straightforward Synthesis of Thiodisaccharides by Ring-Opening of Sugar Epoxides

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2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

inferred← citeshttps://doi.org/10.1021/jp9100448openalex-snapshot

Scanning the Potential Energy Surface of Furanosyl Oxocarbenium Ions: Models for Reactive Intermediates in Glycosylation Reactions

inferred← citeshttps://doi.org/10.1021/ol0510668openalex-snapshot

Acceptor-Dependent Stereoselective Glycosylation: 2‘-CB Glycoside-Mediated Direct β- d -Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall

inferred← citeshttps://doi.org/10.1021/ol051912eopenalex-snapshot

Synthesis of α- d -Idoseptanosyl Glycosides Using an S-Phenyl Septanoside Donor

inferred← citeshttps://doi.org/10.1021/ol052128xopenalex-snapshot

Base-Promoted Rearrangement of Sugar Epoxides to Unsaturated Sugars

inferred← citeshttps://doi.org/10.1021/ol101520qopenalex-snapshot

β-Selective Arabinofuranosylation Using a 2,3-O-Xylylene-Protected Donor

inferred← citeshttps://doi.org/10.1021/ol102112zopenalex-snapshot

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inferred← citeshttps://doi.org/10.1021/ol400931popenalex-snapshot

Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

inferred← citeshttps://doi.org/10.1021/ol401755eopenalex-snapshot

β-Arabinofuranosylation Using 5-O-(2-Quinolinecarbonyl) Substituted Ethyl Thioglycoside Donors

inferred← citeshttps://doi.org/10.1021/ol7019108openalex-snapshot

Stereoselective Synthesis of 2-Deoxy-furanosides from 2,3-Anhydro-furanosyl Thioglycosides

inferred← citeshttps://doi.org/10.1038/ncomms14019openalex-snapshot

[Au]/[Ag]-catalysed expedient synthesis of branched heneicosafuranosyl arabinogalactan motif of Mycobacterium tuberculosis cell wall

inferred← citeshttps://doi.org/10.1038/ncomms14851openalex-snapshot

Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units

inferred← citeshttps://doi.org/10.1039/9781849730891-00038openalex-snapshot

Mycobacterial lipoarabinomannan fragments as haptens for potential anti-tuberculosis vaccines

inferred← citeshttps://doi.org/10.1039/c3cc00042gopenalex-snapshot

Automated solid phase synthesis of oligoarabinofuranosides

inferred← citeshttps://doi.org/10.1039/c3cs35457aopenalex-snapshot

Design of chemical glycosyl donors: does changing ring conformation influence selectivity/reactivity?

inferred← citeshttps://doi.org/10.1039/c3ob40958aopenalex-snapshot

Chemical synthesis of β-arabinofuranosyl containing oligosaccharides derived from plant cell wall extensins

inferred← citeshttps://doi.org/10.1039/c4qo00113copenalex-snapshot

Synthesis of 2-deoxy-C-glycosides via Lewis acid-mediated rearrangement of 2,3-anhydro-1-thiopyranosides

inferred← citeshttps://doi.org/10.1039/d0ob00260gopenalex-snapshot

β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor

inferred← citeshttps://doi.org/10.1039/d4ob01593bopenalex-snapshot

Why is thiol unexpectedly less reactive but more selective than alcohol in phenanthroline-catalyzed 1,2- cis O - and S -furanosylations?

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Synthesis of 2‐Deoxy‐2‐thiophenylglucosyl Azides through 1,2 Thio Migration of Thiophenyl Mannosides

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Recent Advances in the Synthesis of Natural 2-Deoxy-β-glycosides

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Synthesis of Oligosaccharide Fragments of Mannosylated Lipoarabinomannan Appropriately Functionalized for Neoglycoconjugate Preparation

inferred← citeshttps://doi.org/10.1081/car-120025322openalex-snapshot

Synthesis of Oligosaccharide Fragments of Mannosylated Lipoarabinomannan Appropriately Functionalized for Neoglycoconjugate Preparation

inferred← citeshttps://doi.org/10.1081/car-120026604openalex-snapshot

Regioselectivity in Alkylation Reactions of 1,2‐O‐Stannylene Acetals of d ‐Arabinofuranose

inferred← citeshttps://doi.org/10.1081/car-200066978openalex-snapshot

Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*

inferred← citeshttps://doi.org/10.1107/s1600536803012352openalex-snapshot

1-(2′,3′-Anhydro-5′-O-benzoyl-β- D -lyxofuransoyl)-5-fluorouracil

inferred← citeshttps://doi.org/10.1107/s1600536804027266openalex-snapshot

p-Tolyl 2,3-anhydro-5,6-O-isopropylidene-1-thio-β- D -gulofuranoside

inferred← citeshttps://doi.org/10.1134/s1070363218070101openalex-snapshot

Isoniazid Conjugates with D-Arabinofuranose

inferred← citeshttps://doi.org/10.1139/v10-091openalex-snapshot

Configurations and conformations of glycosyl sulfoxides

inferred← citeshttps://doi.org/10.3390/molecules15107235openalex-snapshot

Protecting Groups in Carbohydrate Chemistry: Influence on Stereoselectivity of Glycosylations

inferred← citeshttps://doi.org/10.4052/tigg.23.134openalex-snapshot

Chemical Synthesis of Furanose Glycosides

inferred← citeshttps://doi.org/10.7831/ras.6.1openalex-snapshot

STEREODIRECTING EFFECT OF CYCLIC SILYL PROTECTING GROUPS IN CHEMICAL GLYCOSYLATION

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