4-Methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-ido-pyranosiduronic acid

Base Information

• Chemical Name: 4-Methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-ido-pyranosiduronic acid
• CAS No.: 66966-09-4
• Molecular Formula: C16H16O9
• Molecular Weight: 352.298
• Hs Code.: 2932209090
• European Community (EC) Number: 266-527-5
• DSSTox Substance ID: DTXSID10985697
• Nikkaji Number: J310.173H
• Wikidata: Q82973318
• Mol file: 66966-09-4.mol

Synonyms:4-methylumbelliferyl iduronide;4-methylumbelliferyl-alpha-L-iduronide;4-MUBI

Chemical Property of 4-Methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-ido-pyranosiduronic acid

Chemical Property:

• Melting Point: >112°C (dec.)
• Boiling Point: 683.1oC at 760 mmHg
• Flash Point: 255oC
• PSA: 146.66000
• Density: 1.632g/cm3
• LogP: -0.62760
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 352.07943208
• Heavy Atom Count: 25
• Complexity: 574

Purity/Quality:

98%Min ^*data from raw suppliers

4-Methylumbelliferyl a-L-idopyranosiduronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](O3)C(=O)O)O)O)O
• Uses: 4-Methylumbelliferyl α-L-Iduronide (free acid) is a fluorogenic substrate for α-L-iduronidase. This product form is the free acid, which offers a considerable weight for weight advantage over the 4-MU iduronide salt in terms of its application dose.

Technology Process of 4-Methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-ido-pyranosiduronic acid

There total 13 articles about 4-Methyl-2-oxo-2H-1-benzopyran-7-yl alpha-L-ido-pyranosiduronic acid 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: 83.2%

4-methylcoumarin-7-yl-α-L-iduronic acid methyl ester (128095-52-3) → 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid (66966-09-4,84434-84-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at -10 ℃; for 2h;

Reference yield: 21.0%

1-(4-methylumbelliferone)-α-L-idopyranoside (66901-41-5,39940-54-0) → 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid (66966-09-4,84434-84-4)

Guidance literature:

platinum; In water; at 95 ℃; for 3h;

DOI:10.1016/0008-6215(83)88356-6

Reference yield:

1,2,3,4,6-penta-O-acetyl-α-L-idopyranose (2152-77-4) → 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid (66966-09-4,84434-84-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 38 percent / zinc chloride / 0.75 h / 150 - 155 °C

2: 81 percent / sodium methoxyde / methanol / Ambient temperature

3: 21 percent / platinum black / H₂O / 3 h / 95 °C

With sodium methylate; zinc(II) chloride; platinum; In methanol; water;

DOI:10.1016/0008-6215(83)88356-6

upstream raw materials:

1-(4-methylumbelliferone)-α-L-idopyranoside

1,2,3,4,6-penta-O-acetyl-α-L-idopyranose

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

1-(4-methylumbelliferone)-2,3,4,6-tetra-O-acetyl-α-L-idopyranose