73464-50-3

Usage

Uses

Used in Organic Synthesis:
2,3,4-Tri-O-acetyl-beta-D-glucuronid acid methyl ester is used as an intermediate in the synthesis of various complex organic compounds. Its unique structure allows for selective functionalization and modification, making it a valuable building block in the development of novel molecules with potential applications in pharmaceuticals, materials science, and other fields.
In the Pharmaceutical Industry:
2,3,4-Tri-O-acetyl-beta-D-glucuronid acid methyl ester is used as a key intermediate for the synthesis of glycosaminoglycans and their derivatives, which are essential components of extracellular matrix and have significant implications in various biological processes. These compounds are being explored for their potential therapeutic applications in treating diseases such as cancer, inflammatory disorders, and degenerative conditions.
In the Materials Science Industry:
2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER is also utilized in the development of advanced materials with unique properties, such as self-healing materials, stimuli-responsive hydrogels, and drug delivery systems. Its ability to form complex structures and interact with other molecules makes it a promising candidate for creating innovative materials with tailored properties for specific applications.
In the Chemical Research Industry:
2,3,4-Tri-O-acetyl-beta-D-glucuronid acid methyl ester serves as a valuable research tool for chemists to study the reactivity and functionalization of complex carbohydrate structures. Its use in chemical research contributes to the advancement of our understanding of carbohydrate chemistry and the development of new synthetic strategies and methodologies.

Upstream product

• 861966-16-7 4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 637317-02-3 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2R,4aR,6S,7R,8R,8aS)-7-azido-6-benzoyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75410-50-3 2-(Methyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronosyloxy)-2-phenylacetonitril 
• 78008-87-4 methyl 2,3,4-tri-O-acetyl-1-O-(N-acetyl-L-phenylalanyl)-β-D-glucopyranuronate 
• 78008-93-2 methyl 2,3,4-tri-O-acetyl-1-O-(N-acetyl-L-phenylalanyl)-α-D-glucopyranuronate 
• 78008-88-5 methyl 2,3,4-tri-O-acetyl-1-O--β-D-glucopyranuronate 
• 78008-92-1 methyl 2,3,4-tri-O-acetyl-1-O--α-D-glucopyranuronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 190448-65-8 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 197895-54-8 methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate 
• 184579-76-8 N-(4-methyl-3-chlorophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-26-9 N-(4-methyl-2-chlorophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-35-0 N-(4-methyl-2-bromophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 186653-63-4 N-[2-(t-butyldimethylsilyloxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 

Relevant academic research and scientific papers

Gram scale synthesis of the glucuronide metabolite of ABT-724

A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronicrossed d signate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl- α-d-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl α-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the α-fluoride 16.

Synthesis of chlorophenol red glucuronic acid

This invention provides β-D-Glucuronidase substrates of the formula: wherein R1, R2, and R7-R12 are independently selected from the group consisting of: hydrogen, fluorine, chlorine, bromine, iodine, alkyl, hydroxyl, alkoxy, carboxyl and nitro groups; R3-R6 are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, nitro and amino; and M+ is selected from the group consisting of: proton, lithium, sodium, potassium, magnesium, calcium, barium, and ammonium ion.