5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate

Base Information

• Chemical Name: 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate
• CAS No.: 620987-44-2
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.408
• Mol file: 620987-44-2.mol

Synonyms:5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate

Chemical Property of 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate

There total 6 articles about 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate 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%

2-allyl-6-methoxy-benzoic acid (325172-28-9) + 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-3-hydroxy-3,4,5-trihydrofuran-2-one (620987-43-1) → 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate (620987-44-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol035630v

Reference yield:

(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol (58475-17-5) → 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate (620987-44-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

2.1: copper(I) cyanide; MeLi / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2.2: 83 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.1: 85 percent / acetic acid / H₂O / 3 h / 70 °C

4.1: 81 percent / silver(I) carbonate on Celite / benzene / 1 h / Heating

5.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; carbon tetrabromide; methyllithium; copper(l) cyanide; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;

DOI:10.1021/jo050750x

Reference yield:

7-((1S)-1-methylbut-3-enyl)-(1R,5R,7S)-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]octane (620987-42-0) → 5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-oxo-3,4,5-trihydrofuryl 6-methoxy-2-prop-2-enylbenzoate (620987-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / acetic acid / H₂O / 3 h / 70 °C

2: 81 percent / silver(I) carbonate on Celite / benzene / 1 h / Heating

3: 95 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; acetic acid; dicyclohexyl-carbodiimide; silver carbonate; In dichloromethane; water; benzene;

DOI:10.1021/jo050750x

upstream raw materials:

2-allyl-6-methoxy-benzoic acid

5-((1S)-1-methylbut-3-enyl)-(3R,5S)-3-hydroxy-3,4,5-trihydrofuran-2-one

5-((1S)-1-methylbut-3-enyl)-(3R,5S)-oxolane-2,3-diol

(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

Downstream raw materials:

(1S,3S,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate

(1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate

1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate

(1S,3R,4S)-1-(2-cyanoethyl)-3-(methoxymethoxy)-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate