4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester

Base Information

• Chemical Name: 4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester
• CAS No.: 128095-50-1
• Molecular Formula: C23H24O12
• Molecular Weight: 492.436
• Mol file: 128095-50-1.mol

Synonyms:4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester;4-Methyl-2-oxo-2H-1-benzopyran-7-yl α-L-Idopyranosiduronic Acid Methyl Ester, Triacetate;4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-alpha-L-idopyranosiduronic Acid, Methyl Ester

Chemical Property of 4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester

Chemical Property:

• Melting Point: 112-113 °C
• Boiling Point: 589.6±50.0 °C(Predicted)
• PSA: 153.87000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 1.17320
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

4-Methylumbelliferyl2,3,4-Tri-O-acetyl-α-L-idopyranosiduronicAcid,MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester (cas# 128095-50-1) is a compound useful in organic synthesis.

Technology Process of 4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic Acid, Methyl Ester

There total 6 articles about 4-Methylumbelliferyl 2,3,4-Tri-O-acetyl-α-L-idopyranosiduronic 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: 46.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + methyl 1,2,3,4-tetra-O-acetyl-L-idopyranuronate (3082-95-9,72692-06-9,73464-50-3) → methyl 4-methylcoumarin-7-yl-2,3,4-tri-O-acetyl-α-L-idopyranuronate (1421266-08-1) + 4-methylcoumarin-7-yl-2,3,4-tri-O-acetyl-α-L-iduronic acid methyl ester (128095-50-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h; Molecular sieve; Cooling with ice;

DOI:10.3998/ark.5550190.0014.203

Reference yield:

methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate (101014-65-7) → 4-methylcoumarin-7-yl-2,3,4-tri-O-acetyl-α-L-iduronic acid methyl ester (128095-50-1)

Guidance literature:

methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate; With N-Bromosuccinimide; In tetrachloromethane; for 2h; Reflux; Irradiation;

With triethyl borane; tri-n-butyl-tin hydride; In hexane; dichloromethane; at -78 ℃; for 5h; Inert atmosphere;

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → 4-methylcoumarin-7-yl-2,3,4-tri-O-acetyl-α-L-iduronic acid methyl ester (128095-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver(l) oxide / acetonitrile / 4 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / tetrachloromethane / 2 h / Inert atmosphere; Irradiation; Reflux

2.2: 5 h / -78 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; silver(l) oxide; In tetrachloromethane; acetonitrile;

DOI:10.1055/s-0040-1708021

upstream raw materials:

7-hydroxy-4-methyl-chromen-2-one

methyl 1,2,3,4-tetra-O-acetyl-L-idopyranuronate

methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

4-methylcoumarin-7-yl-α-L-iduronic acid methyl ester

4-methylcoumarin-7-yl α-L-idopyranosiduronic acid

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