2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

Base Information

Chemical Name:2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester
CAS No.:620987-47-5
Molecular Formula:C₂₄H₂₉NO₅
Molecular Weight:411.498
Hs Code.:

Synonyms:2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

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Chemical Property of 2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

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Technology Process of 2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

There total 9 articles about 2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl 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: 97.0%

: 108-24-7
acetic anhydride

: 620987-60-2
2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-1-((E)-2-cyano-vinyl)-3-hydroxy-4-methyl-hept-6-enyl ester

: 620987-47-5
2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

Guidance literature:: With TEA; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol035630v

Reference yield:

: 58475-17-5
(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

: 620987-47-5
2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: CBr₄; PPh₃ / tetrahydrofuran / 0 - 6 °C

1.2: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

2.1: 85 percent / AcOH / H₂O / 3 h / 70 °C

3.1: 81 percent / AgCO₃/Celite / benzene / 1 h / Heating

4.1: 95 percent / DCC / CH₂Cl₂ / 24 h / 20 °C

5.1: 93 percent / DIBAL-H / diethyl ether / 0.5 h / -78 °C

6.1: toluene / 2 h / 80 °C

7.1: 74 percent / DEAD; PPh₃ / toluene / 24 h / -30 - 20 °C

8.1: 95 percent / K₂CO₃ / methanol / 3 h / 20 °C

9.1: 97 percent / TEA / CH₂Cl₂ / 2 h / 20 °C

With silver (II) carbonate; carbon tetrabromide; Celite; TEA; diisobutylaluminium hydride; potassium carbonate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; benzene; 6.1: Wittig olefination;
DOI:10.1021/ol035630v

Reference yield:

: 620987-43-1
5-((1S)-1-methylbut-3-enyl)-(3R,5S)-3-hydroxy-3,4,5-trihydrofuran-2-one

: 620987-47-5
2-Allyl-6-methoxy-benzoic acid (1R,3R,4S)-3-acetoxy-1-((E)-2-cyano-vinyl)-4-methyl-hept-6-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / DCC / CH₂Cl₂ / 24 h / 20 °C

2: 93 percent / DIBAL-H / diethyl ether / 0.5 h / -78 °C

3: toluene / 2 h / 80 °C

4: 74 percent / DEAD; PPh₃ / toluene / 24 h / -30 - 20 °C

5: 95 percent / K₂CO₃ / methanol / 3 h / 20 °C

6: 97 percent / TEA / CH₂Cl₂ / 2 h / 20 °C

With TEA; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In methanol; diethyl ether; dichloromethane; toluene; 3: Wittig olefination;
DOI:10.1021/ol035630v