acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 795306-59-1
• Molecular Formula: C₅₀H₅₅F₂NO₂₀
• Molecular Weight: 1027.98
• Mol file: 795306-59-1.mol

Synonyms:acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 6 articles about acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl 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: 30.0%

3′-(S)-4-(S)-3-(R)-[3′-t-butyldimethylsilyloxy-3′-(4-fluorophenyl)propyl]-4-(4-hydroxyphenyl)-1-(4-fluorophenyl)azetidin-2-one (795306-57-9) + 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate (92052-38-5,106256-81-9,106256-89-7,126736-02-5,132287-70-8,132287-71-9,139403-73-9,130703-21-8) → acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (795306-59-1) + acetic acid 4-acetoxy-6-acetoxymethyl-2-{4-[3-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -37 - 20 ℃; for 2.5h;

DOI:10.1002/anie.200460348

Reference yield:

Acetic acid 4-{(2S,3R)-1-(4-fluoro-phenyl)-3-[(S)-3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenyl ester (795306-53-5) → acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (795306-59-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / imidazole / dimethylformamide / 3 h

2: 83 percent / neutral alumina / CH₂Cl₂ / 5.5 h / 70 °C

3: BF₃*OEt₂ / CH₂Cl₂ / 2.5 h / -37 - 20 °C

With 1H-imidazole; aluminum oxide; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460348

Reference yield:

Acetic acid 4-[(2S,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenyl ester (795306-55-7) → acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (795306-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / neutral alumina / CH₂Cl₂ / 5.5 h / 70 °C

2: BF₃*OEt₂ / CH₂Cl₂ / 2.5 h / -37 - 20 °C

With aluminum oxide; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1002/anie.200460348

upstream raw materials:

3′-(S)-4-(S)-3-(R)-[3′-t-butyldimethylsilyloxy-3′-(4-fluorophenyl)propyl]-4-(4-hydroxyphenyl)-1-(4-fluorophenyl)azetidin-2-one

4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate

Acetic acid 4-{(2S,3R)-1-(4-fluoro-phenyl)-3-[(S)-3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenyl ester

Acetic acid 4-[(2S,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenyl ester

Downstream raw materials:

acetic acid 4-acetoxy-6-acetoxymethyl-2-(4-{1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester