An effective synthesis of α-glycosides of N-acetylneuraminic acid derivatives by use of 2-deoxy-2β-halo-3β-hydroxy-4,7,8,9-tetra-O-acetyl- N-acetylneuraminic acid methyl ester

doi:10.1016/S0040-4020(01)87797-8

Paper

DOI: 10.1016/S0040-4020(01)87797-8

An effective synthesis of α-glycosides of N-acetylneuraminic acid derivatives by use of 2-deoxy-2β-halo-3β-hydroxy-4,7,8,9-tetra-O-acetyl- N-acetylneuraminic acid methyl ester

Published 1987 · K. Okamoto, T. Kondo, T. Goto

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Abstract

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Study Snapshot

This study successfully synthesized NauAc -glycosides from N-acetylneuraminic acid derivatives using 2-deoxy-2-halo-3-hydroxy-4,7,8,9-tetra-O-acetyl-N-acetyln

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Synthese eines trisaccharides aus N-acetylneuraminsäure und N-acetyllactosamin

A trisaccharide containing N-acetylneuraminic acid can be synthesized by combining N-acetylneuraminic acid and N-acetyllactosamin, with a deblocking sequence enabling the isolation of the -linked iso

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An effective synthesis of α-glycosides of -acetylneuraminic acid by use of 2β-halo-3β-hydroxy-4,7,8,9-tetra--acetyl--acetylneuraminic acid methyl ester ☆

This study successfully synthesized -glycosides of -acetylneuraminic acid using 2-halo-3-hydroxy-4,7,8,9-tetra--acetyl--acetylneuraminic acid methyl ester and

1986·37citations·K. Okamoto et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/S0040-4039(00)85176-X

Syntheses of (α2–9) and (α2–8) linked neuraminylneuraminic acid derivatives

This study synthesized (2–9)NeuAc and (2–8)NeuAc linkage neuraminylneuraminic acid derivatives, which are involved in group C meningococcal polysaccharides and gangliosides, in high yields.

1986·42citations·K. Okamoto et al.·Tetrahedron Letters

Tetrahedron Letters

Citations

DOI: 10.1016/j.carres.2022.108543

Practical non-enzymatic synthesis of propargyl sialyl-α-(2-3')-lactosamine trisaccharide using minimal protecting groups manipulation.

Propargyl sialyl--(2-3')-lactosamine trisaccharide can be efficiently synthesized in a few steps using minimal protecting groups manipulation, offering higher yield and steric hindrance compared to previous methods.

2022·1citation·Shuay Abdullayev et al.·Carbohydrate research

Carbohydrate research

DOI: 10.1016/j.bmc.2010.11.067

The effect of structural differences in the reducing terminus of sugars on the binding affinity of carbohydrates and proteins analyzed using photoaffinity labeling.

Closed-ring carbohydrate ligands, with closed reducing sugars, bind to proteins more strongly than open-ring sugars, improving our understanding of carbohydrate-protein interactions.

2011·11citations·I. Ohtsuka et al.·Bioorganic & medicinal chemistry

Bioorganic & medicinal chemistry

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Silylene/Oxazolidinone Double-Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane

Silylene/oxazolidinone double-locked sialic acid building blocks efficiently perform sialylation reactions in chloromethane, providing desired coupling products with excellent -selectivity compared to oxazolidinone-locked building blocks.

2009·35citations·S. Hanashima et al.·European Journal of Organic Chemistry

European Journal of Organic Chemistry

DOI: 10.1016/J.TET.2009.04.022

Phosphite-based sialic acid donors in the synthesis of α(2→9) oligosialic acids

Phosphite-based sialic acid donors with an anomeric thiocresol-protected acceptor provide good -selectivity and yield in sialylation, with potential for efficient synthesis of tetra-sialic acid.

2009·14citations·Chang-Ching Lin et al.·Tetrahedron

Tetrahedron

DOI: 10.1002/EJOC.200800914

BiBr3‐Promoted Activation of Peracetylated Glycosyl Iodides: Straightforward Access to Synthetically Useful 2‐O‐Deprotected Allyl Glycosides

BiBr3-promoted activation of peracetylated glycosyl iodides provides straightforward access to synthetically useful 2'-O-deprotected allyl glycosides, with shorter experimental times and no need for strong acids.

2008·15citations·A. Pastore et al.·European Journal of Organic Chemistry

European Journal of Organic Chemistry