cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone

Base Information

• Chemical Name: cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone
• CAS No.: 133101-74-3
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.214
• Mol file: 133101-74-3.mol

Synonyms:

Chemical Property of cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone

There total 11 articles about cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone 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: 43.0%

methanol (67-56-1) + styrylacetic acid (2243-53-0) → cis-(RR,SS)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone (133101-74-3,133101-75-4)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In acetonitrile; at 60 ℃; for 2h; Inert atmosphere; Electrolysis;

DOI:10.1002/adsc.201801173

Reference yield:

methanol (67-56-1) + methyl anti-3-phenyloxirane-2-acetate → methyl 3-hydroxy-4-methoxy-4-phenylbutanoate + trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone (133101-74-3,133101-75-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 21 ℃; regioselective reaction; Cooling with ice; Inert atmosphere;

DOI:10.1021/ol201378w

Reference yield:

trans-styrylacetic acid (2243-53-0,59744-46-6,1914-58-5) → methyl 3-hydroxy-4-methoxy-4-phenylbutanoate + trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone (133101-74-3,133101-75-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 21 °C / Cooling with ice; Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / chloroform / 20 °C / Cooling with ice; Inert atmosphere

3: boron trifluoride diethyl etherate / dichloromethane / 21 °C / Cooling with ice; Inert atmosphere

With sulfuric acid; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform;

DOI:10.1021/ol201378w

upstream raw materials:

β-methoxy-γ-oxo-γ-phenylbutanoic acid

2-Methoxyacetophenone

4-oxo-4-(2-methoxyphenyl)butyric acid methyl ester

methanol