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

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

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

Downstream Products

• 82187-44-8 1-O-2-(4-Chlorphenoxy)-2-methyl-propionyl-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 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 
• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 869996-05-4 O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate 
• 141796-18-1 (2S,3S,4S,5R,6R)-6-(((2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid 
• 188003-24-9 (4S,5R,6R)-4,5-Diacetoxy-6-benzyloxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 82187-45-9 1-O-(4-Chlorphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat 

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.

Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl- α-d-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl α-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the α-fluoride 16.

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.