20379-61-7

Basic information

• Product Name: a-D-Glucosyl azide, tetraacetate.
• Synonyms: a-D-Glucosyl azide, tetraacetate.
• CAS NO: 20379-61-7
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 0
• Mol File: 20379-61-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 106.5 °C
• Appearance: /
• CAS DataBase Reference: a-D-Glucosyl azide, tetraacetate.(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Glucosyl azide, tetraacetate.(20379-61-7)
• EPA Substance Registry System: a-D-Glucosyl azide, tetraacetate.(20379-61-7)

Safety Data

• Hazardous Substances Data: 20379-61-7(Hazardous Substances Data)

Upstream product

• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 78028-93-0 1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 353264-43-4 1-N-(4-methylbenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 18918-58-6 1-N-(4-chlorobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 18918-52-0 1-N-(4-nitrobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 76051-36-0 2,3,4,6-tetra-O-acetyl-N-(α-ethyl benzyloxycarbonyl-L-aspartyl)-α-D-glucopyranosylamine 
• 106192-40-9 2,3,4-Tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranosylazid 
• 1351610-65-5 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(6-[(R)-(tert-butyldimethylsilyloxy)(phenyl)methyl]-4-methoxypyridin-2-yl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1351610-68-8 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(6-[(R)-hydroxy(phenyl)methyl]-4-methoxypyridin-2-yl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1333231-60-9 C₄₁H₄₉N₉O₂₀ 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 70128-27-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylamine 
• 20379-60-6 α-D-Glucopyranosyl azide 
• 20379-59-3 D-glucopyranosyl azide 
• 1644077-56-4 C₃₄H₄₄N₄O₁₇S 

Relevant articles and documents

UDP-GlcNAc Analogues as Inhibitors of O-GlcNAc Transferase (OGT): Spectroscopic, Computational, and Biological Studies

A series of glycomimetics of UDP-GlcNAc, in which the β-phosphate has been replaced by either an alkyl chain or a triazolyl ring and the sugar moiety has been replaced by a pyrrolidine ring, has been synthesized by the application of different click-chemistry procedures. Their affinities for human O-GlcNAc transferase (hOGT) have been evaluated and studied both spectroscopically and computationally. The binding epitopes of the best ligands have been determined in solution by means of saturation transfer difference (STD) NMR spectroscopy. Experimental, spectroscopic, and computational results are in agreement, pointing out the essential role of the binding of β-phosphate. We have found that the loss of interactions from the β-phosphate can be counterbalanced by the presence of hydrophobic groups at a pyrroline ring acting as a surrogate of the carbohydrate unit. Two of the prepared glycomimetics show inhibition at a micromolar level.

Protecting group free synthesis of urea-linked glycoconjugates: Efficient synthesis of β-urea glycosides in aqueous solution

A method for the protecting group free synthesis of β-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and d-glucose, N-acetyl-d-glucosamine or d-xylose in acidic aqueous solution, furnishes the corresponding β-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of β-urea tethered amino acid-carbohydrate conjugates. This journal is the Partner Organisations 2014.

Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles

Glycosyl 1,2,3-triazoles with α-d-gluco, β-d-gluco, α-d-galacto, β-d-galacto and β-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 β-N-acetylhexosaminidase. β-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors.