72692-06-9

Basic information

• Product Name: 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester
• Synonyms: 2,3,4-TRI-O-ACETYL-D-GLUCURONIC ACID METHYL ESTER;Methyl-(2,3,4-tri-O-acetyl-a-D-glucopyranosyl)uronate
• CAS NO: 72692-06-9
• Molecular Formula: C₁₃H₁₈O₁₀
• Molecular Weight: 334.28
• Product Categories: Carbohydrates & Derivatives;Intermediates
• Mol File: 72692-06-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 103-105?C
• Boiling Point: 401.689°C at 760 mmHg
• Flash Point: 141.543°C
• Appearance: /
• Density: 1.371g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.23±0.70(Predicted)
• Stability: Acid Sensitive
• CAS DataBase Reference: 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester(72692-06-9)
• EPA Substance Registry System: 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester(72692-06-9)

Safety Data

• Hazardous Substances Data: 72692-06-9(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

May contain a minor amount of the beta isomer.

InChI:InChI=1/C13H18O10/c1-5(14)20-8-9(21-6(2)15)11(22-7(3)16)13(18)23-10(8)12(17)19-4/h8-11,13,18H,1-4H3/t8-,9?,10?,11?,13+/m0/s1

Upstream product

• 861966-16-7 4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 92420-79-6 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-benzhydryloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 129878-43-9 methyl (3,4-di-O-acetyl-1,2-(4-bromophenoxy)ethylidene-β-D-glucopyranosid)uronate 
• 129878-42-8 methyl (p-bromophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 129878-42-8 methyl (p-bromophenyl 2,3,4-tri-O-acetyl-α-D-glucopyranosid)uronate 
• 82187-44-8 1-O-2-(4-Chlorphenoxy)-2-methyl-propionyl-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat 
• 129878-44-0 methyl (p-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 129878-44-0 methyl (p-methoxyphenyl 2,3,4-tri-O-acetyl-α-D-glucopyranosid)uronate 
• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 184579-76-8 N-(4-methyl-3-chlorophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 184579-72-4 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-methyl-2-nitro-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 184579-83-7 N-[4-(t-butyldimethylsilyloxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 184579-81-5 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(2'-allyloxycarbonyl-biphenyl-2-ylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 190448-65-8 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 247075-26-9 N-(4-methyl-2-chlorophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 

Relevant articles and documents

Gram scale synthesis of the glucuronide metabolite of ABT-724

A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronicrossed d signate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.

Synthesis of chlorophenol red glucuronic acid

This invention provides β-D-Glucuronidase substrates of the formula: wherein R1, R2, and R7-R12 are independently selected from the group consisting of: hydrogen, fluorine, chlorine, bromine, iodine, alkyl, hydroxyl, alkoxy, carboxyl and nitro groups; R3-R6 are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, nitro and amino; and M+ is selected from the group consisting of: proton, lithium, sodium, potassium, magnesium, calcium, barium, and ammonium ion.