4-ACETAMIDOOPHENYL TRIACETYL-BETA-D-GLUCOPYRANOSIDURONIC ACID, METHYL ESTER

Base Information

• Chemical Name: 4-ACETAMIDOOPHENYL TRIACETYL-BETA-D-GLUCOPYRANOSIDURONIC ACID, METHYL ESTER
• CAS No.: 30824-21-6
• Molecular Formula: C21H25 N O11
• Molecular Weight: 467.43
• Mol file: 30824-21-6.mol

Synonyms:Glucopyranosiduronicacid, p-acetamidophenyl, methyl ester, 2,3,4-triacetate, b-D- (8CI)

Chemical Property of 4-ACETAMIDOOPHENYL TRIACETYL-BETA-D-GLUCOPYRANOSIDURONIC ACID, METHYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 212-213°C dec.
• Boiling Point: 590.477°C at 760 mmHg
• PKA: 14.47±0.70(Predicted)
• Flash Point: 310.909°C
• PSA: 152.76000
• Density: 1.345g/cm³
• LogP: 0.78980
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Acetaminophen metabolites

Technology Process of 4-ACETAMIDOOPHENYL TRIACETYL-BETA-D-GLUCOPYRANOSIDURONIC ACID, METHYL ESTER

There total 8 articles about 4-ACETAMIDOOPHENYL TRIACETYL-BETA-D-GLUCOPYRANOSIDURONIC 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: 76.0%

4-acetaminophenol (103-90-2,8055-08-1) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → methyl <4-(acetamido)phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (30824-21-6)

Guidance literature:

4-acetaminophenol; methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate; In dichloromethane; for 0.5h; Molecular sieve;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1016/j.carres.2011.12.018

Reference yield:

Ketene (463-51-4) + methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (18472-49-6) → methyl <4-(N-hydroxyacetamido)phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (78180-85-5) + methyl <4-(acetamido)phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (30824-21-6)

Guidance literature:

With aluminium amalgam; Yield given. Multistep reaction. Yields of byproduct given; 1.) ether, ethyl acetate, 15-20 deg C, 5 min;

DOI:10.1021/jm00140a014

Reference yield:

O1-(4-amino-phenyl)-β-D-glucopyranuronic acid (21080-66-0) → methyl <4-(acetamido)phenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate (30824-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: acetone; silver oxide

With pyridine; acetone; silver(l) oxide;

upstream raw materials:

diazomethane

acetic anhydride

[14C]-Acetaminophen glucuronide

methyl iodide

Downstream raw materials:

1-O-(4-acetamidophenyl)-β-D-glucopyranuronic acid sodium salt

[14C]-Acetaminophen glucuronide