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

Uses

Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-glucuronide methyl ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death. Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of water-soluble glucuronide derivatives of Camptothecin, which is used for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of glucuronide prodrug compounds of Janus kinase (JAK) inhibitor tofacitinib, which could be cleaved by β-glucuronidase enzymes such as those produced by the microbiome in the gastrointestinal tract, thereby increasing levels of tofacitinib at the site of gastrointestinal inflammation and limiting the systemic exposure of tofacitinib when treating localized inflammatory diseases.

Chemical Properties

White Crystalline Solid

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

• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 63-29-6 D-glucurono-6,3-lactone 
• 77668-10-1 2,3,4-tri-O-acetyl-β-D-glucuronic acid methyl ester 
• 73630-93-0 1-bromo-N,N,2-trimethyl-1-propen-1-amine 
• 18486-47-0 methyl D-galactopyranuronate 
• 108-24-7 acetic anhydride 
• 32449-92-6 D-glucurono-6,3-lactone 
• 65615-69-2 methyl (5R)-1,2,3,4-tetra-O-acetyl-5-C-bromo-β-D-glucopyranuronate 
• 57690-62-7 methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 82228-14-6 methyl D-glucopyranuronate 
• 252000-90-1 methyl (3,4-di-O-tert-butyldimethylsilyl-D-glucuronate)glycal 
• 95530-80-6 methyl 1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 67-56-1 methanol 
• 6556-12-3 D-glucuronic acid 

Downstream Products

• 24459-59-4 Nalorphin-3-yl-ss-D-glucopyranosiduronsaeure 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 162552-89-8 Methyl O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzyl-β-D-glucopyranoside)uronate 
• 172471-47-5 1D-(1,3,5/2,4)-4-acetamido-5-azido-2-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-1-O-pivaloyl-1,2,3-cyclohexanetriol 
• 148580-09-0 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 191352-29-1 (2S,3R,4S,5S,6S)-2-(2-((tert-butoxycarbonyl)(methyl)amino)-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 5432-32-6 methyl 1,2,3,4-tetraacetyl-α-D-glucopyranuronate 
• 201789-31-3 allyl 2-O-benzoyl-β-D-galactopyranoside 
• 202577-46-6 Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate 
• 202577-47-7 Methyl 2,3,4-tri-O-acetyl-1-O-2,6-dinitrobenzyl-β-D-glucopyranuronate 
• 148579-56-0 (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

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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Practical Synthesis of the Fluorogenic Enzyme Substrate 4-Methylumbelliferyl α- L -Idopyranosiduronic Acid

A practical and concise synthesis of 4-methylumbelliferyl α- l -idopyranosiduronic acid, a fluorogenic enzyme substrate diagnostic for α- l -iduronidase, was accomplished. It features successive radical bromination and radical reduction of easily accessible methyl 4-methyl umbelliferyl-2,3,4-tri- O -acetyl-β- d -glucouronate in four steps with 28percent overall yield.

Preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite

The invention relates to a preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite, and belongs to the field of compound preparation. According to the preparation method, glucuronolactone is used as a basic reaction raw material, the ethyl glucuronide of the ethyl alcohol non-oxidative metabolite can be obtained by reacting under ultrasonic, water bath heating and other conditions through a triacetyl bromide glucuronic acid methyl ester intermediate, and the preparation method has the advantages of low environmental factors, simple operation and easyrealization; and in addition, absolute ethyl alcohol and sulfuric acid are used as raw materials, and the ethyl sulfate of the ethyl alcohol non-oxidative metabolite is obtained through heating, filtration, precipitation, water bath evaporating and other operations, and the preparation method has the advantages of wide source of raw materials, low requirements for environmental factors, simple operation and easy realization.