2H-1-Benzopyran-2-one, 7-[[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-4-methyl-

Base Information

• Chemical Name: 2H-1-Benzopyran-2-one, 7-[[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-4-methyl-
• CAS No.: 37067-30-4
• Molecular Formula: C18H21NO8
• Molecular Weight: 379.367
• Hs Code.: 29321900
• European Community (EC) Number: 253-333-0
• DSSTox Substance ID: DTXSID20885659
• Nikkaji Number: J260.729H
• Wikidata: Q72492323
• Mol file: 37067-30-4.mol

Synonyms:4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside;4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside;4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide;4-methylumbelliferyl-N-acetyl-beta-glucosamine;4-methylumbelliferyl-N-acetylglucosaminide;4-MU-Glc-NAc;4-MUAG;MUABG

Chemical Property of 2H-1-Benzopyran-2-one, 7-[[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-4-methyl-

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 1.67E-22mmHg at 25°C
• Melting Point: 208-210 °C
• Refractive Index: 1.632
• Boiling Point: 732.2 °C at 760 mmHg
• PKA: 12.87±0.70(Predicted)
• Flash Point: 396.6 °C
• PSA: 138.46000
• Density: 1.47 g/cm³
• LogP: -0.18520
• Storage Temp.: −20°C
• Solubility.: DMF: 20 mg/mL, clear, colorless
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 379.12671663
• Heavy Atom Count: 27
• Complexity: 608

Purity/Quality:

98%, ^*data from raw suppliers

4-Methylumbelliferyl 2-Acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)O)O)NC(=O)C
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)C
• Uses: 4-METHYLUMBELLIFERYL-N-ACETYL-BETA-D-GLUCOSAMINIDE is used for the assay of b-Acetylglucosaminidase. A fluorogenic substrate used for the diagnosis of GM2 gangliosidoses in leukocytes. Genetic defects in human b-hexosaminidase isozy mes (Hex A & Hex B) result in various clinical and biochemical types of GM2 gangliosidosis. They include Tay Sachs disease, Sandhoff disease and other forms. Fluorescence: max. Abs. l = 325nm, max. Em. l = 378nm 4-Methylumbelliferyl N-acetyl-β-D-glucosaminide has been used as a substrate for assayingβ-N-acetylglucosaminidase (NAGase) from soil sampleschitinase from Fusarium oxysporum using fluorimetric assayβ-N-acetylhexosaminidases from Arabidopsis thaliana roots and leaves samples

Technology Process of 2H-1-Benzopyran-2-one, 7-[[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-4-methyl-

There total 5 articles about 2H-1-Benzopyran-2-one, 7-[[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]oxy]-4-methyl- 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: 96.0%

4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (38971-29-8) → N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (37067-30-4)

Guidance literature:

4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside; With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 4h;

In methanol; dichloromethane;

DOI:10.1016/j.carres.2011.03.042

Reference yield:

4-methylumbelliferyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride → N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (37067-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

2: sodium methoxide / methanol

With sodium methylate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja065697o

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-3-yl]-acetamide (37067-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cesium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 0.17 h / 20 °C

1.2: 0.92 h

2.1: sodium methylate / methanol; dichloromethane / 4 h / 20 °C

2.2: amberlite-H+

With cesium hydroxide; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane; water;

DOI:10.1016/j.carres.2011.03.042

upstream raw materials:

4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

4-methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside

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

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

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

4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(methyl 2,3-di-O-benzoyl-4-deoxy-β-D-glucopyranosyl uronate)-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside

4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(methyl 2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl uronate)-4,6-O-di-tert-butylsilanediyl-β-D-glucopyranoside

N-Acetyl-D-glucosamine

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