(2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 38971-29-8
• Molecular Formula: C24H27NO11
• Molecular Weight: 505.478
• DSSTox Substance ID: DTXSID40560370
• Wikidata: Q82443489
• Mol file: 38971-29-8.mol

Synonyms:38971-29-8;(2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate;124167-45-9;[(2R,3S,4R,5R,6S)-5-Acetamido-3,4-diacetyloxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate;4-Methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;DTXSID40560370;(2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyldiacetate;4-Methyl-2-oxo-2H-1-benzopyran-7-yl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside;4-Methyl-7-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-Beta-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one

Chemical Property of (2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property:

• PSA: 189.67000
• LogP: -0.30920
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 505.15841068
• Heavy Atom Count: 36
• Complexity: 916

Purity/Quality:

98% ^*data from raw suppliers

4-Methyl-7-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one ^*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)COC(=O)C)OC(=O)C)OC(=O)C)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)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Uses: 4-Methyl-7-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one is an intermediate in synthesizing 4-Methylumbelliferyl 2-Acetamido-2-deoxy-β-D-glucopyranoside (M334000). a Fluorogenic substrate 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 isozymes (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

Technology Process of (2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

There total 3 articles about (2R,3S,4R,5R,6S)-5-Acetamido-2-(acetoxymethyl)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 72.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → 4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (38971-29-8)

Guidance literature:

7-hydroxy-4-methyl-chromen-2-one; With cesium hydroxide; tetrabutylammomium bromide; In dichloromethane; water; at 20 ℃; for 0.166667h;

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester; In dichloromethane; water; for 0.916667h;

DOI:10.1016/j.carres.2011.03.042

Reference yield:

4-methylumbelliferyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride + acetyl chloride (75-36-5) → 4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (38971-29-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja065697o

Reference yield:

→ 4-methylumbelliferyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (38971-29-8)

Guidance literature:

aus dem entspr. Glucosylbromid, 4-Methylumbelliferon;

DOI:10.1016/S0008-6215(00)82692-0

upstream raw materials:

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

acetyl chloride

Downstream raw materials:

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

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

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

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