3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester

Base Information

• Chemical Name: 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester
• CAS No.: 190448-56-7
• Molecular Formula: C39H39F2NO13
• Molecular Weight: 767.734
• Mol file: 190448-56-7.mol

Synonyms:3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester;4-[(2S,3R)-3-[(3S)-3-(Acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxo-2-azetidinyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate

Chemical Property of 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester

Chemical Property:

• Boiling Point: 808.9±65.0 °C(Predicted)
• PKA: -0.43±0.60(Predicted)
• PSA: 170.27000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 4.89030
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

3-O-AcetylEzetimibe2,3,4-Tri-O-acetyl-β-D-glucuronideMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Phase-II metabolites of Ezetimibe. Glucuronide azetidinone cholesterol absorption inhibitor.

Technology Process of 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide Methyl Ester

There total 4 articles about 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl--D-glucuronide 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: 95.0%

(1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate (190448-46-5,1044664-24-5) + methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (190448-56-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 10 ℃; for 4h;

DOI:10.1016/S0960-894X(98)00008-0

Reference yield: 52.0%

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) + (1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate (190448-46-5,1044664-24-5) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (190448-56-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃;

DOI:10.1002/anie.200460348

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{4-[(2S,3R)-3-[(S)-3-acetoxy-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (190448-56-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrazine acetate / dimethylformamide / 20 h / 55 °C

2: Cs₂CO₃ / CH₂Cl₂ / 3 h

3: 52 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 - 20 °C

With boron trifluoride diethyl etherate; hydrazinium monoacetate; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460348

upstream raw materials:

(1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propyl acetate

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

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

Downstream raw materials:

[14C]-Ezetimibe glucuronide

Refernces

• 1、 Vacarro, Wayne D.,Davis, Harry R.. "Sugar-Substituted 2-Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar". . p. 313 - 318. Retrieved 2007/10/03.