20298-35-5

Basic information

• Product Name: methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose)
• CAS NO: 20298-35-5
• Molecular Weight: 323.3
• Mol File: 20298-35-5.mol
• Article Data: 101

Chemical Properties

• CAS DataBase Reference: methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose)(CAS DataBase Reference)
• NIST Chemistry Reference: methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose)(20298-35-5)
• EPA Substance Registry System: methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose)(20298-35-5)

Safety Data

• Hazardous Substances Data: 20298-35-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 131-48-6 N-Acetylneuraminic acid 
• 489-46-3 N-acetyl neuraminic acid 
• 6813-81-6 N-acetyl neuraminic acid 
• 19342-33-7 N-acetyl neuraminic acid 
• 335592-15-9 N-acetyl-β-neuraminic acid 1,7-lactone 
• 489-46-3 sialic acid 
• 489-46-3 sialic acid 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 149-73-5 trimethyl orthoformate 
• 74-88-4 methyl iodide 
• 1355952-68-9 (2R,3S,4R,5R,6S)-5-acetamido-3,4-bis(benzoyloxy)-8-(ethoxycarbonyl)non-8-ene-1,2,6-triyl triacetate 
• 124-41-4 sodium methylate 
• 1104460-85-6 N-acetyl-4-O-benzyl-β-neuraminic acid methyl ester 

Downstream Products

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 132883-18-2 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride 
• 771577-91-4 (2S,4S,5R,6R)-5-Acetylamino-6-[(1R,2R)-3-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-1,2-dihydroxy-propyl]-2,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 78850-37-0 methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate 
• 139933-32-7 methyl (4-formylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2 nonulopyranosid)onate 
• 1208104-57-7 methyl (tert-butyl-5-(4-aminophenyl-5-oxopentylcarbamate) 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 1208104-58-8 methyl (5-amino-N-(4-phenyl)pentanamide 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 1208104-59-9 methyl ((tert-butyl-4-benzylamino)butylcarbamate 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 1208104-60-2 methyl (N-(4-benzyl)butane-1,4-diamine 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 59694-37-0 methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 130087-26-2 methyl (4-aminophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 124974-13-6 methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 
• 124925-06-0 methyl (4-aminophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosid)onate 

Relevant articles and documents

SYNTHESES OF 2-O-GLYCOSYL DERIVATIVES OF N-ACETYL-D-NEURAMINIC ACID

Syntheses of N-acetyl-D-neuraminic acid derivatives are reported.Methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-2-chloro-2-deoxy-β-D-neuraminate (3) was prepared directly from methyl N-acetyl-β-D-neuraminate (2) in good yield.Koenigs-Knorr reaction of 3 with an excess of methanol gave the methyl α-glycoside of methyl N-acetyl-D-neuraminate (4). 2,3-O-Isopropylidene-D-ribono-1,4-lactone, 2,3-O-isopropylideneuridine, and 5-fluor-2,3-O-isopropylideneuridine reacted with 3 to give anomeric mixtures of methyl N-acetyl-D-neuraminate derivatives.The stereochemistry of these compounds was confirmed from n.m.r. and c.d. spectra, and measurements of the rate of hydrolysis of the glycosidic bond.

One pot synthesis of thio -glycosides via aziridine opening reactions

A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.

Cooperative Multipoint Recognition of Sialic Acid by Benzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors

Sialic acid recognition remains an interesting and challenging target in molecular receptor design. Herein, we report a series of benzoboroxole-based receptors in which cationic hydrogen-bond donors have been introduced and shown to promote multipoint sialic acid recognition. One striking feature revealed by these receptors is that the carboxylate sialic acid residue is the primary binding determinant for recognition by benzoboroxole, in which the presence of charge-reinforced hydrogen bonds results in enhanced selectivity for sialic acid over other carbohydrates and a 4.5-fold increase in affinity. These findings open up wide possibilities for benzoboroxole-based receptors use in life science research, biotechnology, and diagnostics.