4550-93-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl 2,3,4-Tri-O-benzyl-D-glucuronate Acetate is used as a reactant for the preparation of bile acid 24-acyl glucuronides. These glucuronides are important in the pharmaceutical industry as they are involved in the metabolism and excretion of certain drugs and endogenous compounds, such as bilirubin and steroid hormones. Benzyl 2,3,4-Tri-O-benzyl-D-glucuronate Acetate's role in the synthesis of these glucuronides makes it a valuable intermediate in the development of drugs targeting various health conditions.

Upstream product

• 108-24-7 acetic anhydride 
• 142797-33-9 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 120444-48-6 (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 2595-06-4 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 125474-14-8 benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranuronate 
• 125474-13-7 benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 
• 4539-78-0 2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of bile acid 24-acyl glucuronides

The synthesis of acyl glucuronides of common bile acids is described. By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate, which was prepared from 1-O-methyl-α-D-glucose. The separation and purification of the β2-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benyl group on the sugar moiety was achieved by catalytic hydrogenation with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties.