124167-43-7

Usage

Uses

Used in the Synthesis of Glycosides:
4-MethyluMbelliferyl 3,4,6-tri-O-Acetyl-2-azido-2-deoxy-α-D-galactopyranoside is used as a synthetic intermediate for the production of 4-methylumbelliferyl glycosides. These glycosides are essential in the detection of αand β-D-galactopyranosaminidases, which are enzymes involved in the metabolism of complex carbohydrates.
Used in Enzyme Detection:
In the field of biochemistry and molecular biology, 4-MethyluMbelliferyl 3,4,6-tri-O-Acetyl-2-azido-2-deoxy-α-D-galactopyranoside is used as a substrate for the detection and analysis of αand β-D-galactopyranosaminidases. This application is crucial for understanding the enzymatic processes and their role in various biological systems.
Used in Pharmaceutical Research:
Due to its unique chemical structure, 4-MethyluMbelliferyl 3,4,6-tri-O-Acetyl-2-azido-2-deoxy-α-D-galactopyranoside may also hold potential in the development of new pharmaceutical compounds targeting specific enzymes or biological pathways. Its application in this industry could lead to the discovery of novel therapeutic agents.
Used in Analytical Chemistry:
In the field of analytical chemistry, 4-MethyluMbelliferyl 3,4,6-tri-O-Acetyl-2-azido-2-deoxy-α-D-galactopyranoside can be employed as a reference compound or standard for the calibration of analytical instruments and methods. Its distinct chemical properties make it suitable for this purpose, ensuring accurate and reliable measurements.

Upstream product

• 4098-06-0 triacetyl-D-galactal 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 167939-15-3 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate 
• 67817-41-8 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 

Downstream Products

• 124223-99-0 4-methylumbelliferyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 124167-45-9 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside 

Relevant academic research and scientific papers

A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

A practical and efficient α-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-d-galatosaminyl imidates, with which exclusive α-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl α-T-antigen.

Synthesis of 4-methylumbelliferyl glycosides for the detection of α- and β-D-galactopyranosaminidases

Reaction at room temperature of either 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α- of β-D-galactopyranosyl chloride with a twofold excess of 4-methylumbelliferone and silver trifluoromethanesulfonate in dichloromethane containing an equimolar amount of sym-collidine yielded 4-methylumbelliferyl tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside in 33percent yield.The β anomer was formed in 20 and 10percent yields, respectively.Reduction of the azido group, acetylation followed by de-O-acetylation, provided the desired 4-methylumbelliferyl 2-acetamido-2-deoxy-α- and β-D-galactopyranosides (N-acetyl-α- and β-D-galactopyranosaminides).The α-glycoside proved to be an effective substrate for the highly sensitive fluorimetric detection of N-acetyl-α-D-galactopyranosaminidase activity in human tissues and was used to examine the deficiency of this activity, which is the enzymatic defect in Schindler disease.Key words: synthesis of 4-methylumbelliferyl N-acetyl-α- and β-D-galactopyranosaminides, N-acetyl-α-D-galactosaminidase deficiency (Schindler disease).