7355-18-2

Usage

Uses

Used in Organic Synthesis:
METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE is used as a key intermediate in organic synthesis for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the formation of complex molecules through chemical reactions, making it a valuable component in the synthesis of target compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE is used as a building block for the development of novel drug candidates. Its ability to form complex molecules makes it a promising starting material for the synthesis of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique chemical properties enable the development of innovative products that can effectively protect crops from pests and diseases.
Used in Specialty Chemicals Industry:
In the specialty chemicals industry, METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE is employed as a versatile intermediate for the synthesis of various specialty chemicals, such as dyes, fragrances, and other high-value products. Its ability to form complex molecules contributes to the development of unique and innovative chemical compounds with specific applications.

InChI:InChI=1/C15H20O11/c1-6(16)22-10-11(23-7(2)17)13(24-8(3)18)15(25-9(4)19)26-12(10)14(20)21-5/h10-13,15H,1-5H3

Upstream product

• 110-86-1 pyridine 
• 52613-19-1 glucuronic acid methyl ester 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 186581-53-3 diazomethane 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 62133-77-1 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 
• 65615-69-2 methyl (5R)-1,2,3,4-tetra-O-acetyl-5-C-bromo-β-D-glucopyranuronate 
• 82228-14-6 methyl D-glucopyranuronate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 63-29-6 D-glucurono-6,3-lactone 
• 75-36-5 acetyl chloride 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 

Downstream Products

• 92420-85-4 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate 
• 129878-42-8 O²,O³,O⁴-triacetyl-O¹-(4-bromo-phenyl)-β-D-glucopyranuronic acid methyl ester 
• 18404-55-2 O²,O³,O⁴-triacetyl-O¹-[1]naphthyl-β-D-glucopyranuronic acid methyl ester 
• 4630-61-9 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester 
• 109557-64-4 methyl 1-m-cresyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 
• 82187-45-9 1-O-(4-Chlorphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat 
• 111270-48-5 O²,O³,O⁴-triacetyl-O¹-(4-hydroxy-phenyl)-β-D-glucopyranuronic acid methyl ester 
• 1037310-38-5 1,4-bis(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyloxyuronate)benzene 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 77476-81-4 N¹-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-5-fluorouracil 
• 77476-83-6 N³-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-5-fluorouracil 
• 59495-75-9 O²,O³,O⁴-triacetyl-O¹-(2,2,2-trichloro-ethyl)-β-D-glucopyranuronic acid methyl ester 
• 97337-66-1 methyl 2,3,4-tri-O-acetyl-β-O-cinnamylglucuronate 
• 97337-67-2 methyl 2,3,4-tri-O-acetyl-α-O-cinnamylglucuronate 

Relevant academic research and scientific papers

Synthesis of a Macrocyclic Conjugate of the Diterpenoid Isosteviol and Glucuronic Acid

A macrocyclic conjugate of the natural diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and glucuronic acid was synthesized for the first time. The conjugate contained two molecules of dihydroisosteviol β-D-glucuronoside joined by 1,8-octanedicarboxylate and 1,8-octanedicarbazoyl spacers.

Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains

Novel phosphorylated glycolipids based on glucuronic acid have been synthesized and shown to inhibit M. Tuberculosis H37Rv in vitro at a minimum inhibitory concentration of 12.5 μg/mL.

Bile alcohol glucuronides: Regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol

A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α,7α,12α,25-tetrol-3-O-β-D-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol to methyl (tetra-O-acetyl-β-D-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution 1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomatosis (CTX). A facile and regiocontrolled procedure for the preparation of 5β-cholestane-3α, 7α, 12α, 25-tetrol-3-O-β-D-glucuronide and its corresponding C-26 analogue is described. The method involves direct coupling of bile alcohols, namely, 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α 25-tetrol to methyl (tetra-O-acetyl-β-D-glucopyranuronate) in the presence of a Lewis acid, tin(IV) chloride, in dichloromethane. The resulting anomeric pairs of 1,2-trans- and 1,2-cis-glucuronides of tetrols were resolved by analytical and preparative thin-layer chromatography, and their identities were established by high-resolution 1H NMR spectroscopy and by chemical-ionization and fast-atom-bombardment mass spectrometry. The method described has a practical advantage over the traditional two-step synthesis involving bromides as it is more efficient and uses inexpensive and less toxic materials. It is suggested that these compounds will be useful for studying permeability of the blood-brain barrier in cerebrotendinous xanthomastosis (CTX).

Solid state structure of sodium β-1-thiophenyl glucuronate identifies 5-coordinate sodium with three independent glucoronates

Glucuronic acid is a key component of the glycosaminoglycans (GAGs) Chrondroitin Sulfate (CS), Heparin/Heparan sulfate (HS) and Hyaluronic Acid (HA), as well an important metabolite derivative. In biological systems the carboxylate of uronic acids in GAGs is involved in important H-binding interactions, and the role of metal coordination, such as sodiated systems, has indications associated with a number of biological effects, and physiological GAG-related processes. In synthetic approaches to GAG fragments, thioglycoside intermediates, or derivatives from these, are commonly employed. Of the reported examples of sodium coordination in carbohydrates, 6-coordinate systems are usually observed often with water ligands involved, Herein we report an unexpected 5-coordinate sodiated GlcA crystal structure of the parent GlcA, but as a thioglycoside derivative, whose crystal coordination differs from previous examples, with no involvement of water as a ligand and containing a distorted trigonal bypramidal sodium with each GlcA having five of 6 oxygens sodium-coordinated.

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.

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.

Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists

Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate-protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.

Mirabegron metabolite synthesis method

The invention discloses a mirabegron metabolite synthesis method and belongs to the field of drug metabolism. The mirabegron metabolite synthesis method can prepare a mirabegron metabolite from glucurolactone (1R)-2-2[2-(4-nitrophenyl)ethylamino]-1-phenylethanol as starting materials through eight-step reaction. The mirabegron metabolite synthesis method has the advantages that the synthesis method is reasonable in process design and strong in operability on the basis of optimal preparation steps and reaction conditions screened by a great number of experiments; the synthesis method is high inyield and can reach high chemical purity above 99% and therefore can be applied to industrial production of mirabegron metabolite; the mirabegron metabolite can provide a standard substance for metabolic mechanism research of the mirabegron drug, can be used for exploring the metabolic process of the drugs in vivo, and has high application research value in clinical pharmacokinetic study.

Extended scaffold glucuronides: En route to the universal synthesis of O -aryl glucuronide prodrugs

We demonstrate that an extended scaffold based on a self-immolative linker (SIL) enables the universal production of O-aryl glucuronide prodrugs: high yield glucuronidation is performed on a precursor substrate (SIL) and the subsequent drug conjugation proceeds via less challenging chemical reactions.

A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI

Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.