Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Protecting Groups In Carbohydrate Chemistry: Influence On Stereoselectivity Of Glycosylations

J. Guo, X. Ye
Published 2010 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Saccharides are polyhydroxy compounds, and their synthesis requires complex protecting group manipulations. Protecting groups are usually used to temporarily mask a functional group which may interfere with a certain reaction, but protecting groups in carbohydrate chemistry do more than protecting groups usually do. Particularly, protecting groups can participate in reactions directly or indirectly, thus affecting the stereochemical outcomes, which is important for synthesis of oligosaccharides. Herein we present an overview of recent advances in protecting groups influencing stereoselectivity in glycosylation reactions, including participating protecting groups, and conformation-constraining protecting groups in general.
This paper references
10.1021/JO070229Y
Mechanistic Studies on the Stereoselective Formation of β-Mannosides from Mannosyl Iodides Using α-Deuterium Kinetic Isotope Effects
M. H. El-Badri (2007)
10.1016/J.TETASY.2004.11.042
Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group
Hiroomi Tokimoto (2005)
10.1016/J.TET.2007.05.126
Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni
M. N. Amin (2007)
10.1002/CHIN.200826246
Stereoselective Glycosylations Using Chiral Auxiliaries
J. Kim (2008)
10.1021/JO9606517
Formation of beta-Mannopyranosides of Primary Alcohols Using the Sulfoxide Method.
D. Crich (1996)
10.1016/S0040-4039(03)00673-7
Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation
L. Chen (2003)
10.1002/CHIN.200023211
Highly Diastereoselective α‐Mannopyranosylation in the Absence of Participating Protecting Groups.
D. Crich (2000)
10.1002/ANIE.198201553
Advances in Selective Chemical Syntheses of Complex Oligosaccharides
H. Paulsen (1982)
10.1021/JA029302M
2,3-Anhydro sugars in glycoside bond synthesis. Highly stereoselective syntheses of oligosaccharides containing α-and β-arabinofuranosyl linkages
R. R. Gadikota (2003)
10.1021/OL070449Y
Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates.
D. Crich (2007)
10.1002/CHEM.200600832
Extended applications of di-tert-butylsilylene-directed alpha-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides.
A. Imamura (2006)
10.1021/JO0508999
Stereocontrolled formation of beta-glucosides and related linkages in the absence of neighboring group participation: influence of a trans-fused 2,3-O-carbonate group.
D. Crich (2005)
Stereoselective glycosylations using chiral auxiliaries. In Frontiers in Modern Carbohydrate Chemistry
J H Kim (2007)
10.1002/CHIN.200421186
An Effective Sialylation Method Using N‐Troc‐ and N‐Fmoc‐Protected β‐Thiophenyl Sialosides and Application to the One‐Pot Two‐Step Synthesis of 2,6‐Sialyl‐T Antigen.
M. Adachi (2004)
Recent advances in sialylation
F. F. Liang (2009)
10.1021/OL062198J
Stereoselective synthesis of a fragment of mycobacterial arabinan.
A. Ishiwata (2006)
10.1016/S0065-2318(09)00005-5
Oligosaccharide synthesis: from conventional methods to modern expeditious strategies.
James T. Smoot (2009)
10.1021/jo900176e
Stereoselective Synthesis of alpha(2,9) Di- to Tetrasialic Acids, Using a 5,4-N,O-Carbonyl Protected Thiosialoside.
H. Tanaka (2009)
10.1002/EJOC.200400616
Remote Participation‐Assisted Synthesis of β‐Mannosides
C. D. Meo (2005)
Recent advances in sialylation. Chin
F F Liang (2009)
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/OL034741R
The 4,6-O-[alpha-(2-(2- iodophenyl)ethylthiocarbonyl)benzylidene] protecting group: stereoselective glycosylation, reductive radical fragmentation, and synthesis of beta-D-rhamnopyranosides and other deoxy sugars.
D. Crich (2003)
10.1002/ANIE.200602699
Dialkylphosphates as stereodirecting protecting groups in oligosaccharide synthesis.
T. Yamada (2006)
A highly α-selective glycosylation for the convenient synthesis of repeating α(1→4)-linked N-acetyl-galactosamine units
L. Yang (2010)
10.1016/S0040-4039(02)00584-1
Pure α-linked products can be obtained in high yields in glycosylation with glucosyl trichloroacetimidate donors with a C2 ester capable of neighboring group participation
Y. Zeng (2002)
10.1021/JA00224A060
Armed and disarmed n-pentenyl glycosides in saccharide couplings leading to oligosaccharides
D. R. Mootoo (1988)
10.2174/138527208784577358
DTBS(di-tert-butylsilylene)-directed α-Galactosylation for the Synthesis of Biologically Relevant Glycans
A. Imamura (2008)
10.1055/S-0029-1219943
Direct α-Selective Glycosylations of Acetyl-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol
Yin-Suo Lu (2010)
10.1002/CHIN.200729231
Recent Trends in the Synthesis of O‐Glycosides of 2‐Amino‐2‐deoxysugars
A. F. G. Bongat (2007)
10.1016/J.CARRES.2006.09.002
The use of cyclic bifunctional protecting groups in oligosaccharide synthesis--an overview.
R. Litjens (2007)
10.1021/JA015132M
Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked Glycosides [J. Am. Chem. Soc. 2001, 123 (38), 9461−9462].
K. Benakli (2001)
10.1084/JEM.162.2.573
Human natural anti-alpha-galactosyl IgG. II. The specific recognition of alpha (1----3)-linked galactose residues
U. Galili (1985)
10.2174/138955709787316083
Solid-phase synthesis of oligosaccharide drugs: a review.
M. Dhanawat (2009)
10.1002/ANIE.200460176
Iterative one-pot synthesis of oligosaccharides.
Xuefei Huang (2004)
10.2174/1570179043485448
Sialic Acid Donors: Chemical Synthesis and Glycosylation
Dino K. Ress and Robert J. Linhardt (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)
10.1016/j.carres.2008.04.007
C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.
Cristina De Meo (2008)
10.1016/J.TETLET.2005.03.099
4-Acetoxy-2,2-dimethylbutanoate: a useful carbohydrate protecting group for the selective formation of β-(1→3)-d-glucans.
H. Yu (2005)
10.1016/S0076-6879(06)16024-3
Cell type-specific roles of carbohydrates in tumor metastasis.
S. Chen (2006)
10.1002/CHIN.200405167
Extended Applications and Potential Limitations of Ring‐Fused 2,3‐Oxazolidinone Thioglycosides in Glycoconjugate Synthesis.
R. Kerns (2004)
10.1021/ar100035r
Mechanism of a chemical glycosylation reaction.
D. Crich (2010)
10.1016/S0040-4039(03)01647-2
Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities
A. Imamura (2003)
10.1021/CR990313G
Recent advances in o-sialylation.
G. Boons (2000)
10.1016/J.TET.2005.08.090
Direct and stereoselective synthesis of β-D-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor
Toshifumi Tsuda (2005)
10.1021/jo800971s
Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors.
Johan D. M. Olsson (2008)
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)
10.1016/S0008-6215(03)00099-5
Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis.
M. Takatani (2003)
10.1002/CHIN.200340193
The 4,6‐O‐[α‐(2‐(2‐Iodophenyl)ethylthiocarbonyl)benzylidene] Protecting Group: Stereoselective Glycosylation, Reductive Radical Fragmentation, and Synthesis of β‐D‐Rhamnopyranosides and Other Deoxy Sugars.
D. Crich (2003)
10.1016/S0008-6215(02)00455-X
Remote control of α- or β-stereoselectivity in (1→3)-glucosylations in the presence of a C-2 ester capable of neighboring-group participation
Y. Zeng (2003)
10.2174/138527208784892213
Galactose: A Specifically Recognized, Terminal Carbohydrate Moiety in Biological Processes
E. Walker-Nasir (2008)
Molecules
(2010)
10.1021/ol801833n
Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides.
J. Park (2008)
10.1021/JO0108818
Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.
D. Crich (2002)
10.1002/CHIN.200540189
Factors Affecting Stereocontrol During Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-D-glucosamine.
P. Wei (2005)
10.1021/cr078215f
The chemical neurobiology of carbohydrates.
Heather E. Murrey (2008)
10.1002/CHIN.200703176
On the Influence of the C2—O2 and C3—O3 Bonds in 4,6-O-Benzylidene-Directed β-Mannopyranosylation and α-Glucopyranosylation.
D. Crich (2007)
10.1021/JA047578J
The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?
H. Jensen (2004)
10.1016/J.TETLET.2009.02.146
Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry
A. Ali (2009)
10.1246/CL.1997.389
Highly Stereoselective Synthesis of 2′-Deoxy-α-ribonucleosides and 2-Deoxy-α-C-ribofuranosides by Remote Stereocontrolled Glycosylation
Teruaki Mukaiyama (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)
10.1002/CHIN.199342295
n‐Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of Serendipity
B. Fraser-Reid (1993)
10.1021/JO0526789
Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.
D. Crich (2006)
10.1023/B:GLYC.0000045091.18392.a8
Synthesis of heparin-like oligosaccharides on polymer supports
R. Ojeda (2004)
10.1021/JO970677D
Experimental and Theoretical Evidence of Through-Space Electrostatic Stabilization of the Incipient Oxocarbenium Ion by an Axially Oriented Electronegative Substituent During Glycopyranoside Acetolysis
M. Miljkovic̄ (1997)
10.1039/B704586G
Oligosaccharide assembly by one-pot multi-step strategy.
Y. Wang (2007)
Cell type-specific roles of carbohydrates in tumor metastasis. Methods Enzymol
S Chen (2006)
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)
10.1021/OL061706M
Synthesis of a beta-(1-->3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation.
D. Crich (2006)
10.1016/S0040-4039(03)01707-6
Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis
H. Ando (2003)
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)
10.1021/OL051038P
Efficient Installation of β-Mannosides Using a Dehydrative Coupling Strategy
J. Codée (2005)
10.1126/SCIENCE.291.5512.2370
Glycosylation and the immune system.
P. Rudd (2001)
10.1021/JO962345Z
Direct Synthesis of β-Mannopyranosides by the Sulfoxide Method
David Crich and (1997)
Direct and stereoselective synthesis of α-linked 2deoxyglycosides
J. Park (2008)
Human natural anti-α-galactosyl IgG. II. The specific recognition of α-(1→3)-linked galactose residues
U. Galili (1985)
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. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3
D. Crich (2004)
10.1007/s10719-008-9117-9
Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator
T. Komori (2008)
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)
10.1002/CHIN.199809203
Coupling of Glycal Derived Thioethyl Glycosyl Donors with Glycal Acceptors. An Advance in the Scope of the Glycal Assembly.
P. Seeberger (1998)
10.1002/CHIN.200712200
A Highly Reactive and Stereoselective β‐Mannopyranosylation System: Mannosyl 4‐Pentenoate/PhSeOTf.
Ju Yuel Baek (2007)
10.1016/J.TET.2007.03.128
β-Selective Glucosylation in the Absence of Neighboring Group Participation: Influence of the 3,4-O-Bisacetal Protecting System.
D. Crich (2007)
10.1016/J.BMC.2005.12.037
Synthesis and TNF-alpha inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components.
A. Ishiwata (2006)
10.1016/S0040-4039(00)00941-2
An unusual example of steric buttressing in glycosylation
D. Crich (2000)
10.1021/JA0629817
Practical Approach for the Stereoselective Introduction of β-Arabinofuranosides
Xiangming Zhu (2006)
10.1055/S-2004-817759
An Effective Sialylation Method Using N-Troc- and N-Fmoc-protected β-Thiophenyl Sialosides and Application to the One-pot Two-step Synthesis of 2,6-Sialyl-T Antigen
M. Adachi (2004)
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)
10.1038/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/JA0613613
Stereoselective Synthesis of Oligo-α-(2,8)-Sialic Acids
H. Tanaka (2006)
10.1007/128_2007_124
Automated Solid Phase Oligosaccharide Synthesis
Bastien Castagner (2007)
10.1126/science.1059820
Chemical Glycobiology
C. Bertozzi (2001)
10.1002/ANIE.200461745
Stereoselective glycosylation reactions with chiral auxiliaries.
J. Kim (2005)
10.1002/CHIN.200851185
Highly Direct α-Selective Glycosylations of 3,4-O-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol.
Yin-Suo Lu (2008)
10.1002/anie.200802036
New principles for glycoside-bond formation.
X. Zhu (2009)
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/OL061938L
1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation.
D. Crich (2006)
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)
10.1002/CHIN.200543208
Ethyl 2-Acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-gly copyranoside as a Versatile GlcNAc Donor.
M. Boysen (2005)
10.1002/EJOC.200900543
Silylene/Oxazolidinone Double-Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane
S. Hanashima (2009)
10.1021/JA971239R
Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic Investigation
David Crich and (1997)
10.1021/JO990243D
Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno Series.
D. Crich (1999)
10.1039/b712591g
Pre-activation protocol leading to highly stereoselectivity-controllable glycosylations of oxazolidinone protected glucosamines.
Yiqun Geng (2008)
10.1021/ol101520q
Beta-selective arabinofuranosylation using a 2,3-O-xylylene-protected donor.
A. Imamura (2010)
10.1002/CHIN.201012239
Opportunities and Challenges in Synthetic Oligosaccharide and Glycoconjugate Research
T. Boltje (2010)
10.1021/JO047812O
Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine.
P. Wei (2005)
antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652
10.1002/CHIN.200542208
2‐O‐Propargyl Ethers: Readily Cleavable, Minimally Intrusive Protecting Groups for β‐Mannosyl Donors.
D. Crich (2005)
10.1002/CHIN.200750199
Direct Stereocontrolled Synthesis of 3-Amino-3-deoxy-β-Mannopyranosides: Importance of the Nitrogen Protecting Group on Stereoselectivity.
D. Crich (2007)
10.1021/JA052548H
A general strategy for stereoselective glycosylations.
J. Kim (2005)
10.1021/JA072892+
Synthesis of the docosanasaccharide arabinan domain of mycobacterial arabinogalactan and a proposed octadecasaccharide biosynthetic precursor.
M. Joe (2007)
10.1021/ol801190c
Highly Direct alpha-Selective Glycosylations of 3,4-O-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol.
Yin-Suo Lu (2008)
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)
10.1002/ANIE.200502694
Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis.
James T. Smoot (2005)
J. Am. Chem. Soc
(1997)
10.1016/J.CARRES.2005.11.032
Isolation and structural characterization of an immunostimulating polysaccharide from fuzi, Aconitum carmichaeli.
C. Zhao (2006)
10.1021/jo7023398
Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation.
D. Crich (2008)
10.1002/CHIN.200603264
Strategies of Synthetic Methodologies for Constructing β‐Mannosidic Linkage
E. S. E. Ashry (2006)
10.1002/CHIN.200842232
DTBS(Di-tert-butylsilylene)-Directed α-Galactosylation for the Synthesis of Biologically Relevant Glycans
A. Imamura (2008)
10.1126/SCIENCE.1058899
Toward Automated Synthesis of Oligosaccharides and Glycoproteins
P. Sears (2001)



This paper is referenced by
10.3389/fbioe.2020.00740
Immobilization of the Highly Active UDP-Glucose Pyrophosphorylase From Thermocrispum agreste Provides a Highly Efficient Biocatalyst for the Production of UDP-Glucose
Antje Kumpf (2020)
10.1002/9783527697014.CH1
Protecting Group Strategies in Carbohydrate Chemistry
A. Volbeda (2019)
C-glycoside synthesis towards innovation in antimicrobials
Patrícia Ferreira Calado (2020)
10.1002/ejoc.202000650
Synthesis and Conformational Analysis of 2‐O‐Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides
Ajaz Ahmed (2020)
Synthesis and characterization of organotriethoxysilanes based on carbohydrates for functional mesoporous organosilica hybrids
A. Marta (2016)
10.1021/jo302178f
o-Xylylene protecting group in carbohydrate chemistry: application to the regioselective protection of a single vic-diol segment in cyclodextrins.
P. Balbuena (2013)
10.1039/d0ob02192j
Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides.
Javeed Ur Rasool (2020)
10.1039/C5RA03276H
1,1-Dioxothiomorpholines with asymmetric environments: protecting group directed diastereoselectivity of glyco divinyl sulfone cyclization
Atanu Bhaumik (2015)
10.1039/d0ob01402h
Stereoselective synthesis of a branched α-decaglucan.
Q. Zhao (2020)
10.1021/acs.joc.7b00065
Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene
Dina Lloyd (2017)
10.1007/978-3-319-77706-1_5
Carbohydrate Modifiers for Tissue Engineering Scaffolds
Kieran L Hudson (2018)
10.1055/S-0036-1591915
Photodeprotection of up to Eight Photolabile Protecting Groups from a Single Glycan
M. Samarasimhareddy (2018)
10.1021/jo502186f
Application of 2-substituted benzyl groups in stereoselective glycosylation.
S. Buda (2015)
10.1021/ol403396j
Hydrogen-bond-mediated aglycone delivery: focus on β-mannosylation.
S. Pistorio (2014)
10.1016/j.cis.2016.11.002
Nano-carbohydrates: Synthesis and application in genetics, biotechnology, and medicine.
A. Jebali (2017)
10.3762/bjoc.9.9
Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C
Abhishek Santra (2013)
10.1016/j.carres.2011.03.012
Studies on the stereoselective synthesis of a protected α-D-Gal-(1→2)-D-Glc fragment.
L. Chen (2011)
10.1002/anie.201301662
Catalytic regioselective oxidation of glycosides.
Manuel Jaeger (2013)
10.1016/J.TETLET.2015.11.052
Super arming of a glycosyl donor using a molecular lever
J. Olsen (2016)
10.2174/1570178615666181022145338
Cu-Fe Spinels: First Heterogeneous and Magnetically Recoverable Catalyst for the Ferrier Rearrangement of 2-Nitroglycals
Leticia Lafuente (2019)
10.1016/j.carres.2014.06.025
Glycosyl alkoxythioimidates as building blocks for glycosylation: a reactivity study.
Sneha C. Ranade (2015)
10.1016/J.TETLET.2013.09.014
The development of N-aryl trifluoroacetimidate-based benzyl and allyl protecting group reagents
Sinele B. Tsabedze (2013)
10.1002/SLCT.201601918
Concise Synthesis of a Pentasaccharide Repeating Unit Corresponding to the O‐Antigen of Salmonella Enterica O51
Ishani Bhaumik (2017)
10.3390/molecules23071742
Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs
Simon S Park (2018)
10.1002/anie.201405084
Hydrogen bond mediated aglycone delivery: synthesis of linear and branched α-glucans.
J. P. Yasomanee (2014)
10.1016/J.CPLETT.2019.03.022
Deacetylation of per-acetatylated glycopyranosides: An overall pattern for acidic catalyzis
R. T. Nasibullin (2019)
10.1016/J.TETLET.2017.08.043
Organotin-catalyzed regioselective benzylation of carbohydrate trans-diols
Hengfu Xu (2017)
10.3390/molecules19056683
Direct 2,3-O-Isopropylidenation of α-d-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
R. Jiang (2014)
10.1021/acs.orglett.6b03683
Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Anomeric Hydroxyl Groups and a Controlled Reduction of the Glycosyl Ester Products.
H. Wang (2017)
10.1016/J.TET.2018.06.014
NMR characterization of α- and β-mannopyranurono-2,6-lactones
Kazuki Tohda (2018)
10.1002/9783527696239.CH2
Application of Armed, Disarmed, Superarmed, and Superdisarmed Building Blocks in Stereocontrolled Glycosylation and Expeditious Oligosaccharide Synthesis
M. Bandara (2017)
10.1039/c7cc00689f
Protecting patches in colloidal synthesis of Au semishells.
D. Mann (2017)
See more
Semantic Scholar Logo Some data provided by SemanticScholar