21085-72-3

Basic information

• Product Name: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER
• Synonyms: ACETOBROMO-A-D-GLUCURONIC ACID, METHYL ESTER;methyl tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucopyranuronate;1-BROMO-2,3,4-TRI-O-ACETYL-ALPHA-D-GLUCURONIC ACID METHYL ESTER; Methyl a-Acetobromoglucuronate;Bromo-2,3,4-tri-O-acetyl-a-d-glucopyranuronic Acid Methyl Ester;(2,3,4-tri-o-acetyl-α-d-glucopyranosyl bromide)uronic acid methyl ester;acetobromo-α-d-glucuronic acid methyl ester;1-Bromo-2,3,4-tri-O-acetyl-a-D-glucuronidemethylester
• CAS NO: 21085-72-3
• Molecular Formula: C₁₃H₁₇BrO₉
• Molecular Weight: 397.17
• EINECS: 244-203-4
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;carbohydrate
• Mol File: 21085-72-3.mol
• Article Data: 59

Chemical Properties

• Melting Point: 80-110 °C(lit.)
• Boiling Point: 388.6 °C at 760 mmHg
• Flash Point: 188.8 °C
• Appearance: White to gray/Crystalline Powder or Solid
• Density: 1.52
• Vapor Pressure: 3.02E-06mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: −20°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly, Heated, Sonicated), Dichlorometha
• Stability: Moisture and Temperature Sensitive
• BRN: 96281
• CAS DataBase Reference: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(21085-72-3)
• EPA Substance Registry System: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(21085-72-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-8-10-21
• Hazardous Substances Data: 21085-72-3(Hazardous Substances Data)

Usage

Description

ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is a white crystalline solid that serves as an essential intermediate in the synthesis of various pharmaceutical compounds. It is a modified form of glucuronic acid, featuring a bromine atom and a methyl ester group, which contribute to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is used as a synthetic intermediate for the development of HMR1098-S-glucuronide methyl ester, a novel K-ATP-blocking agent. ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is being researched for its potential in preventing sudden cardiac death.
Used in Cancer Treatment:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is utilized in the synthesis of water-soluble glucuronide derivatives of Camptothecin. These derivatives are employed in cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT), enhancing the targeted delivery and efficacy of Camptothecin in cancer treatment.
Used in Inflammatory Disease Treatment:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is also used in the synthesis of glucuronide prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib. These prodrugs can be cleaved by β-glucuronidase enzymes, such as those produced by the microbiome in the gastrointestinal tract. This targeted release increases the levels of tofacitinib at the site of gastrointestinal inflammation while limiting systemic exposure, making it a more effective treatment for localized inflammatory diseases.

InChI:InChI=1/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3

Upstream product

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 5432-32-6 methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 186581-53-3 diazomethane 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 82228-14-6 methyl D-glucopyranuronate 
• 63-29-6 D-glucurono-6,3-lactone 
• 28817-88-1 methyl α-D-glucopyranuronate 
• 18486-47-0 methyl D-galactopyranuronate 
• 40269-24-7 methyl (1,2,3,4-tetra-O-acetyl-α,β-D-galactopyranosid) uronate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 108-24-7 acetic anhydride 

Downstream Products

• 92420-85-4 4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate 
• 59495-73-7 p-nitrobenzyl-2,3,4-tri-O-acetyl-beta-D-glucuronic acid methyl ester 
• 29587-10-8 2,3,4-Tri-O-acetyl-1-mercaptomethyl-β-D-glucopyranuronsaeure-methylester 
• 27537-72-0 methyl {(17-oxo-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 
• 122174-73-6 tri-O-acetyl-S-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-1-thio-β-D-glucopyranuronic acid methyl ester 
• 605-72-1 3,5-diiodo-O-((5S)-tri-O-acetyl-5-methoxycarbonyl-β-D-xylopyranosyl)-N-trifluoroacetyl-L-tyrosin-ethyl ester 
• 4630-61-9 2,3,4-tri-O-acetyl-1-O-phenyl-β-D-glucopyranuronic acid methyl ester 
• 62812-42-4 methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate 
• 19237-59-3 methyl 2,3,4-tri-O-acetyl-1-O-benzoyl-β-D-glucopyranuronate 
• 71797-18-7 O²,O³,O⁴-triacetyl-O¹-salicyloyl-β-D-glucopyranuronic acid methyl ester 
• 55325-18-3 O²,O³,O⁴-triacetyl-O¹-(2-acetyl-phenyl)-β-D-glucopyranuronic acid methyl ester 
• 113091-67-1 tri-O-acetyl-1-(N-ethyl-anilino)-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 96622-76-3 2,3,4-Tri-O-acetyl-1-desoxy-1-(phenylamino)-β-D-glucopyranuronsaeure-methylester 
• 113091-68-2 tri-O-acetyl-1-(N-methyl-anilino)-1-deoxy-β-D-glucopyranuronic acid methyl ester 

Relevant articles and documents

Synthesis and positive inotropic activity evaluation of liguzinediol metabolites

2,5-Dihydroxymethyl-3,6-dimethylpyrazine (liguzinediol) has been recently discovered as a potential agent for treatment of heart failure with low safety risk. In the present study, four main metabolites of liguzinediol were synthesized and their positive inotropic activities were evaluated. Synthetic compounds were identical with the isolated metabolites of liguzinediol. Pharmacological examinations showed that the four major metabolites were not observed positive inotropic activity, and revealed that the positive inotropic activity of liguzinediol was essentially attributed to the parent agent.

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.

Intermediates in the synthesis of LaetrileTM: the crystal and molecular structures of methyl (2,3,4-tri-O-acetyl-α-D-glucosyl bromide)uronate and methyl (ethyl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate

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Chemical synthesis of 5’-β-glycoconjugates of vitamin B6

Various 5’-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to KOENIGS-KNORR conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5’-β-[13C6]-labeled pyridoxine glucoside (PNG) was prepared starting from [13C6]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5’-β-pyridoxal glucoside (PLG).

COMPOUNDS, COMPOSITIONS, METHODS, AND USES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS

The present disclosure provides novel polypeptide-therapeutic compound or hormone-therapeutic compound conjugates using cleavable or non-cleavable linkers, whereby the polypeptide or hormone serves to target specific cells using receptor expression on the targeted cell to bind the ligand (polypeptide or hormone) carrying the therapeutic compound unlike antibody drug conjugates. Upon binding, the ligand and the therapeutic compound (multiples of the therapeutic compound in some embodiments) enter the cell by receptor-mediated endocytosis, and release drugs conjugated to the ligand by linkers, to interact with intracellular components to enhance, restore, or block a signal transduction process. The ligands for the polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: cytokines, growth factors and hormones among other proteins with corresponding cell surface specific receptors. The disorders targeted by such polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: immunological disorders (e.g., allergy and autoimmune disorders) and cancer.