4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate

Base Information

• Chemical Name: 4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate
• CAS No.: 918158-55-1
• Molecular Formula: C34H36O14
• Molecular Weight: 0
• Mol file: 918158-55-1.mol

Synonyms:4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate;Methyl (4’-O-Hexanoyldaidzein-7-yl--D-2’’,3’’,4’’-tri-O-acetylglucopyranosid)urinate

Chemical Property of 4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate

Chemical Property:

• PSA: 180.17000
• LogP: 4.01750
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

97% ^*data from raw suppliers

Methyl(4’-O-Hexanoyldaidzein-7-yl-β-D-2’’,3’’,4’’-tri-O-acetylglucopyranosid)urinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: An intermediate for the synthesis of Daidzein 7-?D-Glucuronide An intermediate for the synthesis of Daidzein 7-β-D-Glucuronide.

Technology Process of 4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate

There total 5 articles about 4-Oxo-3-[4-[(1-oxohexyl)oxy]phenyl]-4H-1-benzopyran-7-yl -D-Glucopyranosiduronic Acid Methyl Ester, 2,3,4-Triacetate 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: 81.0%

(2S,3S,4S,5R)-3,4,5-Triacetoxy-6-[2,2,2-trifluoro-N-(4-methoxy-phenyl)-acetimidoyloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester + 4'-O-hexanoyl-daidzein (602329-51-1) → methyl (4'-O-hexanoyldaidzein-7-yl β-D-2'',3'',4''-triacetylglucopyranosid)uronate (918158-55-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2006.10.034

Reference yield: 81.0%

C22H24F3NO11 (918158-52-8) + 4'-O-hexanoyl-daidzein (602329-51-1) → methyl (4'-O-hexanoyldaidzein-7-yl β-D-2'',3'',4''-triacetylglucopyranosid)uronate (918158-55-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.200800803

Reference yield:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) → methyl (4'-O-hexanoyldaidzein-7-yl β-D-2'',3'',4''-triacetylglucopyranosid)uronate (918158-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / 3 h / 20 °C

2: 81 percent / BF₃*EtO₂; 4 Angstroem molecular sieves / CH₂Cl₂ / 6 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; potassium carbonate; In dichloromethane; acetone;

DOI:10.1016/j.tetlet.2006.10.034

upstream raw materials:

4'-O-hexanoyl-daidzein

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

daidzein

Hexanoyl chloride

Downstream raw materials:

Daidzein O₇-glucuronide

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