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

General Description

1,2,3,4-Tetra-O-acetyl-α-D-glucuronide methyl ester is a chemical compound primarily used in pharmaceutical applications and biochemical research. As an acetylated derivative of glucuronic acid, this compound finds usage in creating substances that require an acetylated glucuronic acid component or interacting with aspects of the body's metabolic functions. It is notable for its role in synthesis involved in conjugation reactions, a key process in drug metabolism and elimination. There's limited information available on its safety, making it crucial to handle it under controlled laboratory conditions while adhering to safety guidelines.

Upstream product

• 110-86-1 pyridine 
• 52613-19-1 glucuronic acid methyl ester 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 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 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 32449-92-6 D-glucurono-6,3-lactone 
• 67-56-1 methanol 
• 487-44-5 D-(+)-glucuronic acid γ-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 
• 57690-62-7 methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 197895-54-8 methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate 
• 190448-57-8 [14C]-Ezetimibe glucuronide 
• 190448-56-7 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 864160-21-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[2-(benzyl-methyl-amino)-propyl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 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 

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.