151073-01-7

Basic information

• Product Name: 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-α-D-glucopyranoside
• Synonyms: 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-α-D-glucopyranoside
• CAS NO: 151073-01-7
• Molecular Weight: 373.32
• Mol File: 151073-01-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-α-D-glucopyranoside(151073-01-7)
• EPA Substance Registry System: 1,2,4,6-tetra-O-acetyl-3-azido-3-deoxy-α-D-glucopyranoside(151073-01-7)

Safety Data

• Hazardous Substances Data: 151073-01-7(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 104875-44-7 3-azido-3-deoxy-D-glucopyranose 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 2595-05-3 Diacetone D-glucose 
• 27581-57-3 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 485810-08-0 5-O-(3-azido-2,4,6-tri-O-acetyl-3-deoxy-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine 

Relevant articles and documents

Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose

An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides

A new and facile procedure was developed to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6′-modified)-mycaminose 14-membered ketolides were obtained to verify the utility of the method.

Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase

This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was obtained by Cu(I)-catalysed azide-alkyne cycloaddition reaction ('click chemistry') between the azido-functionalized sugars 1-N3-Gal (commercial), 6-N 3-Gal, 3-N3-Glc and 3-N3-Gul with the corresponding alkyne-based 2-propynyl-sialic acid, as well as by click chemistry reaction between the amino acid N3-ThrOBn with 3-O-propynyl-GalOMe. The 1,2,3-triazole linked sialic acid-6-O-galactose and the sialic acid-galactopyranoside showed high Trypanosoma cruzi trans-sialidase (TcTS) inhibitory activity at 1.0 mM (approx. 90%), whilst only the former displayed relevant trypanocidal activity (IC50 260 μM). These results highlight the 1,2,3-triazole linked sialic acid-6-O-galactose as a prototype for further design of new neoglycoconjugates against Chagas' disease.