5432-32-6

Basic information

• Product Name: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester
• Synonyms: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester;3,4,5,6-tetraacetoxytetrahydropyran-2-carboxylic acid methyl ester;methyl 3,4,5,6-tetraacetyloxyoxane-2-carboxylate;Methyl(1,2,3,4-tetra-O-acetyl-.alpha.-D-glucopyranosid)uronate;(2R,3R,4S,5S,6S)-6-(Methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;Methyl 1,2,3,4-tetra-O-acetyl-alpha-D-glucopyranuronate;(2S,3S,4S,5R,6R)-methyl 3,4,5,6-tetraacetoxy-tetrahydro-2H-pyran-2-carboxylate;TETRA-O-ACETYL-BETA-D-GLUCOPYRANURONSAEURE-METHYLESTER
• CAS NO: 5432-32-6
• Molecular Formula: C₁₅H₂₀O₁₁
• Molecular Weight: 376.31
• Mol File: 5432-32-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 108-120 °C
• Boiling Point: 412.3°Cat760mmHg
• Flash Point: 178.4°C
• Appearance: /
• Density: 1.33g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester(5432-32-6)
• EPA Substance Registry System: 1,2,3,4-Tetra-O-acetyl-a-D-glucuronidemethylester(5432-32-6)

Safety Data

• Hazardous Substances Data: 5432-32-6(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetra-O-acetyl-α-D-glucuronide methyl ester is a chemical compound derived from glucuronic acid, featuring acetyl groups attached to its four hydroxyl groups and a methyl ester group. This acetylated derivative is significant in pharmaceutical applications and biochemical research, particularly for its role in synthesis and conjugation reactions that are integral to drug metabolism and elimination processes.

Uses

Used in Pharmaceutical Applications:
1,2,3,4-Tetra-O-acetyl-α-D-glucuronide methyl ester is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its acetylated glucuronic acid component is essential for creating substances that interact with the body's metabolic functions, facilitating drug metabolism and elimination.
Used in Biochemical Research:
In the field of biochemical research, 1,2,3,4-Tetra-O-acetyl-α-D-glucuronide methyl ester serves as a valuable tool for studying conjugation reactions. These reactions are crucial for understanding how the body processes and eliminates drugs, providing insights into drug design and optimization.
Safety Considerations:
Due to limited information on the safety of 1,2,3,4-Tetra-O-acetyl-α-D-glucuronide methyl ester, it is imperative to handle this compound under controlled laboratory conditions. Adherence to safety guidelines is crucial to ensure the well-being of researchers and the integrity of experiments.

Upstream product

• 52613-19-1 glucuronic acid methyl ester 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 82228-14-6 methyl D-glucopyranuronate 
• 201789-29-9 allyl 2,6-di-O-benzoyl-β-D-galactopyranoside 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 74-88-4 methyl iodide 
• 63-29-6 D-glucurono-6,3-lactone 
• 124-41-4 sodium methylate 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 67-56-1 methanol 
• 6556-12-3 D-glucuronic acid 
• 1190935-89-7 D-glucurono-6,3-lactone 
• 32449-92-6 D-glucurono-6,3-lactone 

Downstream Products

• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 174264-48-3 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-{6-(tert-butyl-dimethyl-silanyloxy)-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 174264-49-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 940867-21-0 C₂₄H₂₉NO₉S₂ 
• 940867-20-9 methyl 2,3,4-tri-O-acetyl-1-(3-phenoxybenzyl)-β-D-glucopyranouronate 
• 65658-93-7 1-(3-phenoxybenzyl)-β-D-glucuronide 
• 67776-38-9 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 14365-73-2 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester 
• 1350467-71-8 methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 
• 52173-67-8 methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 1350467-75-2 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-76-3 C₁₇H₁₅⁽²⁾H₂Cl₃O₈ 
• 1350467-77-4 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate 
• 1350467-78-5 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate 

Relevant articles and documents

Methyl tetra-O-acetyl-α-D-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomer

Methyl tetra-O-acetyl-β-D-glucopyranuronate (1) and methyl tetra-O-acetyl-α-D-glucopyranuronate (3) were isolated as crystalline solids and their crystal structures were obtained. That of the β anomer (1) was the same as that reported by Root et?al., while anomer (3) was found to crystallise in the orthorhombic space group P212121with two independent molecules in the asymmetric unit. No other crystal forms were found for either compound upon recrystallisation from a range of solvents. The α anomer (3) was found to be an impurity in initially precipitated batches of β-anomer (1) in quantities a crystallographic direction in the absence of the α impurity, while the presence of the α anomer (3) enhanced this elongation.

Crystal structure of methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate

The identity of the crystalline product formed by the acetylation of a mixture of methyl α- and β-D-glucopyranuronates has been confirmed as being methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate (3), which agrees with the assignment from 1H NMR. The absolute configuration of compound 3 was assigned to agree with the known chirality of the precursor sugar, D-glucono-6,3-lactone.

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles

Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.

Indole-glucoside substrate and preparation method and application thereof in detection of aerobe vaginitis (AV)

The invention discloses a glycosyl donor synthetic process, aiming to overcome defects in detection of aerobe vaginitis (AV) by the prior art. Glycosyl donor is connected with chromogen indole to generate glucosides, and an indole-glucoside substrate with good effect, high flexibility, high stability and high specificity is then synthetized. According to inspection standards, as a comparison result between the color rendering property of the synthetized substrate and that of conventional AV detection reagents, the color rendering property of the substrate is superior to that of a Chromagar AVdetection reagent. With innovation of the glycosyl donor synthetic process and the synthetic process of gluocosides by connection for synthesis of the indole-glucoside chromogenic substrate, innovation of extraction and purification and application verification, reaction yield of each stage of products is increased greatly, the products are white nearly, influence from color of the substrate to identification process is reduced, and flexibility and accuracy of AV detection are both improved greatly.