diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate

Base Information

• Chemical Name: diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate
• CAS No.: 700380-75-2
• Molecular Formula: C₁₅H₂₂ClO₆P
• Molecular Weight: 364.763
• Mol file: 700380-75-2.mol

Synonyms:diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate

Chemical Property of diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate

There total 4 articles about diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate 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: 44.0%

diethyl 1-chloro-2-oxo-4-butyryloxy-4-(4-methoxyphenyl)butylphosphonate (700380-65-0) → diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate (700380-75-2) + diethyl (4S)-1-chloro-2-oxo-4-butyryloxy-4-(4-methoxyphenyl)butylphosphonate (700380-70-7)

Guidance literature:

With magnesium chloride; Candida rugosa lipase; In di-isopropyl ether; water; at 30 ℃; for 48h;

DOI:10.1016/j.tet.2004.02.073

Reference yield:

[1-chloro-4-hydroxy-4-(4-methoxy-phenyl)-2-oxo-butyl]-phosphonic acid diethyl ester (700380-39-8) → diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate (700380-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; DMAP / CH₂Cl₂ / -10 - 0 °C

2: Candida rugosa lipase; H₂O / diisopropyl ether

With dmap; water; dicyclohexyl-carbodiimide; Candida rugosa lipase; In dichloromethane; di-isopropyl ether;

DOI:10.1055/s-2004-831193

Reference yield:

chloro-1 oxo-2 propylphosphonate de diethyle (101300-08-7) → diethyl (4R)-1-chloro-2-oxo-4-hydroxy-4-(4-methoxyphenyl)butylphosphonate (700380-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / n-butyllithium; sodium hydride / tetrahydrofuran; hexane / 1 h / -78 °C

2: 82 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / -10 - 0 °C

3: 39 percent / Candida rugosa lipase; MgCl₂ / diisopropyl ether; H₂O / 48 h / 30 °C

With dmap; n-butyllithium; sodium hydride; dicyclohexyl-carbodiimide; magnesium chloride; Candida rugosa lipase; In tetrahydrofuran; hexane; dichloromethane; di-isopropyl ether; water;

DOI:10.1016/j.tet.2004.02.073

upstream raw materials:

diethyl 1-chloro-2-oxo-4-butyryloxy-4-(4-methoxyphenyl)butylphosphonate

[1-chloro-4-hydroxy-4-(4-methoxy-phenyl)-2-oxo-butyl]-phosphonic acid diethyl ester

chloro-1 oxo-2 propylphosphonate de diethyle

4-methoxy-benzaldehyde