Online citations, reference lists, and bibliographies.
← Back to Search

Recent Developments In The Construction Of Cis‐Glycosidic Linkages

A. E. Christina, G. V. D. Marel, Jeroen D. C. Codée
Published 2013 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
This paper references
10.1080/07328303.2011.624284
Mannuronic Acids: Reactivity and Selectivity
Jeroen D. C. Codée (2011)
10.1002/EJOC.200600440
Stereoselective Glycosylations Using (R)- or (S)-(Ethoxycarbonyl)benzyl Chiral Auxiliaries at C-2 of Glycopyranosyl Donors
J. Kim (2006)
10.1021/ol2016862
Mannopyranosyl uronic acid donor reactivity.
Marthe T. C. Walvoort (2011)
10.1021/ar100035r
Mechanism of a chemical glycosylation reaction.
D. Crich (2010)
10.1021/JO0522963
Stereoselective C-glycosylation reactions of pyranoses: the conformational preference and reactions of the mannosyl cation.
Claudia G. Lucero (2006)
10.1021/JO981944Y
Theoretical Study of 1-Methoxy-2-sulfanylethan-1-yl Cation: Insight into Intermediates in Glycosidation Reactions
Timothy J. Dudley (1999)
10.1021/JA052548H
A general strategy for stereoselective glycosylations.
J. Kim (2005)
10.1016/j.carres.2008.09.006
Synthesis of beta-D-arabinofuranosides: stereochemical differentiation between D- and L-enantiomers.
Y. Wang (2008)
10.1021/JA061594U
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-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasac
D. Crich (2006)
10.1021/JO061713O
2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to α-d-Galactofuranosides
Y. Bai (2006)
10.1002/chem.200900064
Evidence for endocyclic cleavage of conformationally restricted glycopyranosides.
Shino Manabe (2009)
10.1021/JA993366O
Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers
J. Romero (2000)
10.1038/nchem.1404
Dissecting the Mechanisms of a Class of Chemical Glycosylation Using Primary 13C Kinetic Isotope Effects
M. Huang (2012)
10.1021/JA0629817
Practical Approach for the Stereoselective Introduction of β-Arabinofuranosides
Xiangming Zhu (2006)
10.1021/CR990313G
Recent advances in o-sialylation.
G. Boons (2000)
10.1016/J.CARRES.2006.10.021
Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars.
A. F. G. Bongat (2007)
10.1021/OL070513B
Stereoselective glycosylations of 2-azido-2-deoxy-glucosides using intermediate sulfonium ions.
J. Park (2007)
10.1021/OL034528V
Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.
J. Codée (2003)
10.1021/JA064787Q
Stereocontrolled synthesis of beta-D-mannuronic acid esters: synthesis of an alginate trisaccharide.
L. J. van den Bos (2006)
10.1021/JA0613613
Stereoselective Synthesis of Oligo-α-(2,8)-Sialic Acids
H. Tanaka (2006)
10.1021/JA037935A
Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.
Leticia Ayala (2003)
10.1021/JO971046M
A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds
A. Mico (1997)
10.1016/J.TET.2008.03.103
Stereoselectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol
Yiqun Geng (2008)
10.1021/jo8020192
The stereodirecting effect of the glycosyl C5-carboxylate ester: stereoselective synthesis of beta-mannuronic acid alginates.
J. Codée (2009)
10.1021/JA0111481
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.
D. Crich (2001)
10.1016/S0040-4020(98)00426-8
Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates
D. Crich (1998)
10.1021/JA062531E
N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation.
Shino Manabe (2006)
10.1039/C2SC00940D
Streamlined access to conjugation-ready glycans by automated synthesis
Lenz Kröck (2012)
10.1021/jo101779v
Mannosazide methyl uronate donors. Glycosylating properties and use in the construction of β-ManNAcA-containing oligosaccharides.
Marthe T C Walvoort (2010)
10.1021/JA047578J
The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?
H. Jensen (2004)
10.1021/ja109932t
Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall.
A. Ishiwata (2011)
10.1126/SCIENCE.1057324
Automated Solid-Phase Synthesis of Oligosaccharides
O. Plante (2001)
10.1002/asia.200800406
Synthesis of alginate oligosaccharides containing L-guluronic acids.
Fa-Chen Chi (2009)
10.1021/JA971067Y
Direct Glycosylations with 1-Hydroxy Glycosyl Donors using Trifluoromethanesulfonic Anhydride and Diphenyl Sulfoxide
B. A. Garcia (1997)
10.1021/jo800971s
Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors.
Johan D. M. Olsson (2008)
10.1002/chem.200800960
Stereoselective synthesis of L-guluronic acid alginates.
J. Dinkelaar (2008)
10.1021/OL0342305
Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation.
D. Crich (2003)
10.1021/OL0510668
Acceptor-dependent stereoselective glycosylation: 2'-CB glycoside-mediated direct beta-D-arabinofuranosylation and efficient synthesis of the octaarabinofuranoside in mycobacterial cell wall.
Y. Lee (2005)
10.1021/OL049380+
Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.
L. J. van den Bos (2004)
10.1016/S0040-4039(99)01203-4
Stereoselective 1,2-cis-galactosylation assisted by remote neighboring group participation and solvent effects
A. Demchenko (1999)
10.1021/JA993595A
Dehydrative Glycosylation with Activated Diphenyl Sulfonium Reagents. Scope, Mode of C(1)-Hemiacetal Activation, and Detection of Reactive Glycosyl Intermediates
Brian A. Garcia and (2000)
10.1021/JO047812O
Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine.
P. Wei (2005)
10.1016/J.TETLET.2006.12.061
Application of 4,5-O,N-oxazolidinone protected thiophenyl sialosyl donor to the synthesis of α-sialosides
M. Farris (2007)
10.1038/nchem.663
Chiral auxiliary mediated 1,2-cis glycosylations for the solid supported synthesis of a biologically important branched α-glucan
T. Boltje (2010)
10.1021/ol801548k
Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.
D. Crich (2008)
10.1021/ja201024a
Endocyclic cleavage in glycosides with 2,3-trans cyclic protecting groups.
H. Satoh (2011)
10.1021/jo801630m
Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.
D. Crich (2008)
10.1039/B503651H
Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glycopyranoside as a versatile GlcNAc donor.
M. Boysen (2005)
10.1039/c1cc11680k
Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation.
Yuyong Ma (2011)
10.1002/chem.200902460
Synthesis of monomeric and dimeric repeating units of the zwitterionic type 1 capsular polysaccharide from Streptococcus pneumoniae.
Xiangyang Wu (2010)
10.1039/c2cc17623h
β-Rhamnosides from 6-thio mannosides.
A. E. Christina (2012)
10.1021/JO061417B
On the Influence of the C2−O2 and C3−O3 Bonds in 4,6-O-Benzylidene-Directed β-Mannopyranosylation and α-Glucopyranosylation
D. Crich (2006)
10.1021/JO062431R
O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.
D. Crich (2007)
10.1021/JO9910482
Highly diastereoselective alpha-mannopyranosylation in the absence of participating protecting groups.
D. Crich (2000)
10.1039/b913308a
Stereoselective glycosylation using oxathiane glycosyl donors.
M. Fascione (2009)
10.1021/ja907252u
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 mannopyranosylations.
Ju Yuel Baek (2009)
10.1021/ja3018187
Stereoselective assembly of complex oligosaccharides using anomeric sulfonium ions as glycosyl donors.
T. Fang (2012)
10.1021/JA0349610
2,3-anhydrosugars in glycoside bond synthesis. NMR and computational investigations into the mechanism of glycosylations with 2,3-anhydrofuranosyl glycosyl sulfoxides.
C. Callam (2003)
10.1021/jo201179p
Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-β-D-mannopyranosyl uronates.
Marthe T. C. Walvoort (2011)
10.1021/jo900662v
Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions.
J. Dinkelaar (2009)
10.1021/ja905008p
Equatorial anomeric triflates from mannuronic acid esters.
M. T. Walvoort (2009)
10.1021/jo8022439
Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.
D. Crich (2009)
10.1007/128_2010_111
Uronic acids in oligosaccharide and glycoconjugate synthesis.
J. Codée (2011)
10.1002/chem.200903035
Highly alpha-selective sialyl phosphate donors for efficient preparation of natural sialosides.
Che-Hsiung Hsu (2010)
10.1002/9783527621644
Handbook of Chemical Glycosylation
A. Demchenko (2008)
10.1002/anie.201108744
Automated solid-phase synthesis of β-mannuronic acid alginates.
Marthe T C Walvoort (2012)
10.2533/CHIMIA.2011.59
Synthesis of the beta-rhamnopyranosides and the 6-deoxy-beta-mannoheptopyranosides.
S. Picard (2011)
10.1016/j.carres.2008.04.007
C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.
Cristina De Meo (2008)
10.1021/JO010823M
Diastereoselective nucleophilic substitution reactions of oxasilacyclopentane acetals: application of the "inside attack" model for reactions of five-membered ring oxocarbenium ions.
Teresa J. Bear (2002)
10.1021/jo3002084
Lewis acids as α-directing additives in glycosylations by using 2,3-O-carbonate-protected glucose and galactose thioglycoside donors based on preactivation protocol.
Yiqun Geng (2012)
10.1002/anie.200802036
New principles for glycoside-bond formation.
X. Zhu (2009)
10.1021/OL016869J
Thioglycosides protected as trans-2,3-cyclic carbonates in chemoselective glycosylations.
T. Zhu (2001)
10.1021/ja00029a007
Molecular mechanical investigations of the properties of oxocarbenium ions. 1. Parameter development
R. Woods (1992)
1-ベンゼンスルフィニルピペリジン/トリフルオロメタンスルホン酸無水物 チオグリコシドのグリコシルトリフラートへの低温変換及び種々の異なるグリコシド結合生成用の貯蔵安定性のある試薬の強力な組合せ | 文献情報 | J-GLOBAL 科学技術総合リンクセンター
D. Crich (2001)
10.1002/chem.201101889
Do glycosyl sulfonium ions engage in neighbouring-group participation? A study of oxathiane glycosyl donors and the basis for their stereoselectivity.
M. Fascione (2012)
10.1007/128_2010_102
Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-o-benzylidene protected mannopyranosyl donors and related species.
Sylvain Aubry (2011)
10.1021/OL062198J
Stereoselective synthesis of a fragment of mycobacterial arabinan.
A. Ishiwata (2006)
10.1002/ANIE.200453688
Mechanism of 4,6‐O‐Benzylidene‐Directed β‐Mannosylation as Determined by α‐Deuterium Kinetic Isotope Effects
D. Crich (2004)
10.1021/JO061440X
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 method.
D. Crich (2007)
10.1021/JA0162109
Oxazolidinone protected 2-amino-2-deoxy-D-glucose derivatives as versatile intermediates in stereoselective oligosaccharide synthesis and the formation of alpha-linked glycosides.
K. Benakli (2001)
10.4052/TIGG.23.134
Chemical Synthesis of Furanose Glycosides
A. Imamura (2011)
10.1016/J.TET.2003.11.084
Chemoselective glycosylations using sulfonium triflate activator systems
J. Codée (2004)
10.1038/nchem.399
Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.
Thomas J Boltje (2009)
10.1021/jo102363d
Galacturonic acid lactones in the synthesis of all trisaccharide repeating units of the zwitterionic polysaccharide Sp1.
A. E. Christina (2011)
10.1021/JO070669P
Synthesis of a natural oligosaccharide antibiotic active against Helicobacter pylori.
Shino Manabe (2007)
10.1002/ANIE.200461745
Stereoselective glycosylation reactions with chiral auxiliaries.
J. Kim (2005)
10.1021/OL050491Y
Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis.
L. J. van den Bos (2005)
10.1021/JA063247Q
Mechanistic studies and methods to prevent aglycon transfer of thioglycosides.
Z. Li (2006)
10.1021/JA0375176
Nucleophilic additions to fused bicyclic five-membered ring oxocarbenium ions: evidence for preferential attack on the inside face.
D. M. Smith (2003)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar