Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation

scientific article published on April 17, 2003

Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/OL0342305
P953full work available at URLhttps://pubs.acs.org/doi/pdf/10.1021/ol0342305
P698PubMed publication ID12688743

P50authorDavid CrichQ74971587
P2093author name stringA. U. Vinod
P2860cites workBiological roles of oligosaccharides: all of the theories are correctQ29616459
Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivaQ33423429
Synthesis of glycoproteinsQ34113788
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
Oxazolidinone protected 2-amino-2-deoxy-D-glucose derivatives as versatile intermediates in stereoselective oligosaccharide synthesis and the formation of alpha-linked glycosidesQ43741204
Solid-phase synthesis of beta-mannosidesQ44076642
Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective GlycosylationsQ57242567
Convenient Synthesis of 2-Azido-2-deoxy-aldoses by Diazo TransferQ59796167
Highly diastereoselective alpha-mannopyranosylation in the absence of participating protecting groupsQ73798991
Toward Fully Synthetic Homogeneous Glycoproteins: A High Mannose Core Containing Glycopeptide Carrying Full H-Type 2 Human Blood Group Specificity This work was supported by the National Institutes of Health (Grant nos.: HL-25848 and CA-28824 (to S.Q73882502
Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno SeriesQ77051361
Glycobiology: Toward Understanding the Function of SugarsQ77646225
P433issue8
P407language of work or nameEnglishQ1860
P921main subjectorganic chemistryQ11351
biochemistryQ7094
P304page(s)1297-1300
P577publication date2003-04-01
2003-04-17
P1433published inOrganic LettersQ2396276
P1476titleOxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation
Oxazolidinone Protection of N-Acetylglucosamine Confers High Reactivity on the 4-Hydroxy Group in Glycosylation
P478volume5

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cites work (P2860)
Q57630129A Urea-Linked Glucosamine Dimer as a Building Block for the Synthesis of Linear and Cyclic Neosaccharides
Q38324450A peptide nucleic acid-aminosugar conjugate targeting transactivation response element of HIV-1 RNA genome shows a high bioavailability in human cells and strongly inhibits tat-mediated transactivation of HIV-1 transcription
Q41276894Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivity
Q42236654Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series
Q36013472Iterative one-pot syntheses of chitotetroses
Q35549359Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry
Q43210893O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring
Q42408885Synthesis of 6-PEtN-α-D-GalpNAc-(1->6)-β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof
Q41896543The influence of acceptor nucleophilicity on the glycosylation reaction mechanism
Q46830847The intriguing dual-directing effect of 2-cyanobenzyl ether for a highly stereospecific glycosylation reaction

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