Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry

scientific article published on 4 October 2011

Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/JO2017026
P932PMC publication ID3215858
P698PubMed publication ID21919522
P5875ResearchGate publication ID51644403

P50authorDavid CrichQ74971587
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Indirect cation-flow method: flash generation of alkoxycarbenium ions and studies on the stability of glycosyl cations.Q64895858
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Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in GlycosylationQ73252298
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Highly diastereoselective alpha-mannopyranosylation in the absence of participating protecting groupsQ73798991
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Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limitQ33727064
Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives.Q34167167
Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivativeQ34185785
The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group: a new alcohol protecting group, fully orthogonal with the p-methoxybenzyl group and removable under desilylation conditionsQ35007946
Thioglycosides in sequential glycosylation strategiesQ36229467
The use of cyclic bifunctional protecting groups in oligosaccharide synthesis--an overviewQ36606411
Oversulfated chondroitin sulfate: impact of a heparin impurity, associated with adverse clinical events, on low-molecular-weight heparin preparationQ37071056
The chemical neurobiology of carbohydratesQ37152815
C-5 modifications in N-acetyl-neuraminic acid: scope and limitationsQ37153070
The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ionsQ37171066
Intramolecular aglycon deliveryQ37183226
Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosidesQ37228308
Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.Q37322664
Formation of beta-Mannopyranosides of Primary Alcohols Using the Sulfoxide MethodQ74823657
Stereospecific Synthesis of beta-D-Fructofuranosides Using the Internal Aglycon Delivery ApproachQ74823667
Chemistry of 1-Alkoxy-1-glycosyl Radicals: Formation of beta-Mannopyranosides by Radical Decarboxylation and Decarbonylation of manno-Heptulosonic Acid Glycoside DerivativesQ74823870
N-(phenylthio)-epsilon-caprolactam: a new promoter for the activation of thioglycosidesQ76384648
Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno SeriesQ77051361
Intramolecular o-glycoside bond formationQ77366942
Capsular polysaccharide of Streptococcus pneumoniae type 19F: synthesis of the repeating unitQ77589869
Efficient Sialylation with Phenyltrifluoroacetimidates as Leaving GroupsQ79136609
A highly reactive and stereoselective beta-mannopyranosylation system: mannosyl 4-pentenoate/PhSeOTfQ79236350
Stereoselective synthesis of a fragment of mycobacterial arabinanQ79361416
N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylationQ80117208
Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. TotalQ80259797
Efficient installation of beta-mannosides using a dehydrative coupling strategyQ80375351
Acceptor-dependent stereoselective glycosylation: 2'-CB glycoside-mediated direct beta-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wallQ80375355
Synthesis and glycosylation of a series of 6-mono-, di-, and trifluoro S-phenyl 2,3,4-tri-O-benzyl-thiorhamnopyranosides. Effect of the fluorine substituents on glycosylation stereoselectivityQ80857913
Approximate H(5) Ring Conformation of 2,3-O-Carbonate Protected α- and β-L-Rhamnopyranosides as Confirmed by X-Ray CrystallographyQ81306556
A new, powerful glycosylation method: activation of thioglycosides with dimethyl disulfide-triflic anhydrideQ81384253
Deoxy sugars: occurrence and synthesisQ81430383
2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donorsQ81759107
Mechanism of chemical O-glycosylation: from early studies to recent discoveriesQ82593878
Convergent total synthesis of (+)-TMC-151C by a vinylogous Mukaiyama aldol reaction and ring-closing metathesisQ83174779
Chemistry and glycobiologyQ83899971
Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalystQ84754582
Theoretical Investigation of Solvent Effects on Glycosylation Reactions: Stereoselectivity Controlled by Preferential Conformations of the Intermediate Oxacarbenium-Counterion ComplexQ86825563
Synthesis of β-Mannosides via Prearranged GlycosidesQ88520201
A stereoselective approach for the synthesis of alpha-sialosidesQ43695809
2-(Hydroxycarbonyl)benzyl glycosides: a novel type of glycosyl donors for highly efficient beta-mannopyranosylation and oligosaccharide synthesis by latent-active glycosylationQ43721921
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 linkagesQ43734476
Stereoselective synthesis of beta-L-rhamnopyranosides.Q43821242
Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl beta-D-mannopyranoside, an unusual beta-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesisQ43905716
Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an alpha-xylopyranosyl sulfoxide dependent on the configuration at sulfur.Q44001802
Solid-phase synthesis of beta-mannosidesQ44076642
Stereoselective synthesis of beta-D-mannopyranosides with reactive mannopyranosyl donors possessing a neighboring electron-withdrawing groupQ44119877
Deoxygenation of carbohydrates by thiol-catalysed radical-chain redox rearrangement of the derived benzylidene acetalsQ44556917
The 3,4-O-Carbonate Protecting Group as a β-Directing Group in Rhamnopyranosylation in Both Homogeneous and Heterogeneous Glycosylations As Compared to the Chameleon-like 2,3-O-CarbonatesQ44629731
Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium Ions: Evidence for Preferential Attack on the Inside FaceQ44644757
Electrostatic interactions in cations and their importance in biology and chemistryQ44964854
The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?Q44998762
Mechanism of 4,6-O-benzylidene-directed beta-mannosylation as determined by alpha-deuterium kinetic isotope effectsQ45093014
One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-beta-thiophenyl sialosideQ45174424
Structural evidence that alkoxy substituents adopt electronically preferred pseudoaxial orientations in six-membered ring dioxocarbenium ionsQ45190411
6-O-Benzyl- and 6-O-silyl-N-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxyglucosides: effective glycosyl acceptors in the glucosamine 4-OH Series. effect of anomeric stereochemistry on the removal of the oxazolidinone groupQ45260461
Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions.Q45986286
Stereoselective Synthesis of alpha(2,9) Di- to Tetrasialic Acids, Using a 5,4-N,O-Carbonyl Protected Thiosialoside.Q46026799
Efficient dehydrative sialylation of C-4-aminated sialyl-hemiketal donors with Ph2SO/Tf2O.Q46157903
The two-conformer hypothesis: 2,3,4,6-tetra-O-methyl-mannopyranosyl and -glucopyranosyl oxacarbenium ionsQ46393568
Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donorsQ46422465
Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamineQ46474104
Reagent switchable stereoselective beta(1,2) mannoside mannosylation: OH-2 of mannose is a privileged acceptorQ46479195
Stereoselective direct glycosylation with anomeric hydroxy sugars by activation with phthalic anhydride and trifluoromethanesulfonic anhydride involving glycosyl phthalate intermediatesQ46557702
Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistanceQ46576245
Probing the mechanism of sulfoxide-catalyzed hemiacetal activation in dehydrative glycosylationQ46599682
New principles for glycoside-bond formationQ37378687
Opportunities and challenges in synthetic oligosaccharide and glycoconjugate researchQ37477221
Computational studies of the role of glycopyranosyl oxacarbenium ions in glycobiology and glycochemistryQ37510057
Stereocontrolled synthesis of mannans and rhamnansQ37510066
Recent advances in the synthesis of 2-deoxy-glycosidesQ37588901
The repertoire of glycan determinants in the human glycomeQ37597905
Glycosidase inhibition: assessing mimicry of the transition stateQ37672358
The impact of oxacarbenium ion conformers on the stereochemical outcome of glycosylations.Q37719987
Uronic acids in oligosaccharide and glycoconjugate synthesis.Q37827441
Effect of electron-withdrawing protecting groups at remote positions of donors on glycosylation stereochemistryQ37828097
Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-o-benzylidene protected mannopyranosyl donors and related speciesQ37829376
Carbohydrate chemistry in drug discoveryQ37853437
Synthesis of the beta-rhamnopyranosides and the 6-deoxy-beta-mannoheptopyranosides.Q37862182
The First Total Synthesis of 6-Sulfo-de-N-acetylsialyl Lewis(x) Ganglioside: A Superior Ligand for Human L-SelectinQ38330011
Aiming for the ideal synthesisQ39864855
Acid-Catalyzed Hydrolysis of GlycosidesQ39980009
Benzyne arylation of oxathiane glycosyl donorsQ40587864
Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivityQ41276894
A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonateQ41276957
Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranQ41774744
On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylationQ41828063
Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting groupQ41842610
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 beta-arabinofuranosides: importance of the activation methodQ41846658
Dimethylthexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranoside, dimethylthexylsilyl 3,4,6-tri-O-benzyl-beta-D-mannopyranosyl-(1-->4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranoside, and dimeQ41905748
Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethaneQ41985350
alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialosideQ42033416
1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylationQ42118221
Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylationQ42142589
Dehydrative sialylation with C2-hemiketal sialyl donorsQ42166017
Electrochemical generation of glycosyl triflate poolsQ42632594
Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donorsQ42704172
Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentationQ42734123
Computational study of the influence of cyclic protecting groups in stereoselectivity of glycosylation reactionsQ42975958
Recent advances in stereoselective glycosylation through intramolecular aglycon delivery.Q43002750
Mechanism of a chemical glycosylation reactionQ43055773
Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharidesQ43069778
Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediatesQ43145506
4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitationsQ43149036
Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groupsQ43149052
Highly alpha-selective sialyl phosphate donors for efficient preparation of natural sialosidesQ43196732
4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation: the 2-deoxy-2-fluoro and 3-deoxy-3-fluoro series of donors and the importance of the O2-C2-C3-O3 interactionQ43203297
Direct stereocontrolled synthesis of 3-amino-3-deoxy-beta-mannopyranosides: importance of the nitrogen protecting group on stereoselectivityQ43203304
O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ringQ43210893
Beta-directing effect of electron-withdrawing groups at O-3, O-4, and O-6 positions and alpha-directing effect by remote participation of 3-O-acyl and 6-O-acetyl groups of donors in mannopyranosylationsQ43243599
Stereoselective glycosylation using oxathiane glycosyl donorsQ43269969
Synthesis of potassium (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible soluteQ43289617
Equatorial anomeric triflates from mannuronic acid estersQ43296529
Direct stereoselective synthesis of beta-thiomannosidesQ43503122
P433issue22
P407language of work or nameEnglishQ1860
P304page(s)9193-9209
P577publication date2011-10-04
P1433published inJournal of Organic ChemistryQ898967
P1476titleMethodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry
P478volume76

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