2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER

Base Information

• Chemical Name: 2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER
• CAS No.: 73464-50-3
• Molecular Formula: C₁₃H₁₈O₁₀
• Molecular Weight: 334.28
• Mol file: 73464-50-3.mol

Synonyms:2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER;2,3,4-Tri-O-acetyl-D-glucuronidemethylester

Chemical Property of 2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER

Chemical Property:

• Boiling Point: 401.7±45.0 °C(Predicted)
• PKA: 11.23±0.70(Predicted)
• PSA: 134.66000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: -1.32830
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

2,3,4-Tri-O-acetyl-D-glucuronide methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4-Tri-O-acetyl-D-glucuronide methyl ester (cas# 73464-50-3) is a compound useful in organic synthesis.

Technology Process of 2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER

There total 3 articles about 2,3,4-TRI-O-ACETYL-BETA-D-GLUCURONIC ACID METHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

p-Coumaric Acid (7400-08-0,50940-26-6) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → methyl 1-O-[2'(E)-3'-(4''-hydroxyphenyl)-2'-propenoyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2005.06.029

Reference yield: 23.0%

→ 2-monochlorophenol (95-57-8) + 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester (3082-95-9,72692-06-9,73464-50-3)

Guidance literature:

Reference yield:

4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester (861966-16-7) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → 4-[5-((2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yloxy)-pyridin-2-yl]-piperazine-1-carboxylic acid benzyl ester (915207-11-3) + methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -60 - 23 ℃; for 41h; Title compound not separated from byproducts;

DOI:10.1021/jo0611972

upstream raw materials:

p-Coumaric Acid

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

4-(5-hydroxypyridin-2-yl)piperazine-1-carboxylic acid benzyl ester

Downstream raw materials:

4-(methyl)phenyl-beta-D-glucopyranosiduronic acid methyl ester tetraacetate

(2S,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-p-tolyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

2-(Methyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronosyloxy)-2-phenylacetonitril

methyl 2,3,4-tri-O-acetyl-1-O-(N-acetyl-L-phenylalanyl)-β-D-glucopyranuronate

Refernces

• 1、 Pearson, Andrew G.,Kiefel, Milton J.,Ferro, Vito,Von Itzstein, Mark. "Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid". . p. 2077 - 2085. Retrieved 2007/10/03.