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

Base Information

• Chemical Name: 1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate
• CAS No.: 865622-43-1
• Molecular Formula: C₂₄H₂₉NO₅
• Molecular Weight: 411.498

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate 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%

acetic anhydride (108-24-7) + 1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate (865622-40-8) → 1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate (865622-43-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo050750x

Reference yield:

5-((1S)-1-methylbut-3-enyl)-(3R,5S)-oxolane-2,3-diol (865622-38-4) → 1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate (865622-43-1)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 95 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 93 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C

4: 21 percent / toluene / 2 h / 80 °C

5: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; silver carbonate; In diethyl ether; hexane; dichloromethane; toluene; benzene; 4: Wittig reaction;

DOI:10.1021/jo050750x

Reference yield:

(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol (58475-17-5) → 1-((1S)-1-methylbut-3-enyl)-(1S,3R)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl acetate (865622-43-1)

Guidance literature:

Multi-step reaction with 8 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

6.1: 93 percent / DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C

7.1: 21 percent / toluene / 2 h / 80 °C

8.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

With dmap; carbon tetrabromide; methyllithium; copper(l) cyanide; diisobutylaluminium hydride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 7.1: Wittig reaction;

DOI:10.1021/jo050750x

upstream raw materials:

acetic anhydride

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

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:

1-[(2S)-4-cyano-2-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)butyl]-(1R,2S)-2-methylpent-4-enyl 4-nitrobenzoate

(8E)-(3S,5R,6S)-3-(2-cyanoethyl)-14-hydroxy-6-methyl-1-oxo-2,3,4,5,6,7,10-heptahydrobenzo[f][12]-annulen-5-yl 4-nitrobenzoate

(8E)-(3S,5R,6S)-3-(2-cyanoethyl)-14-methoxy-6-methyl-1-oxo-2,3,4,5,6,7,10-heptahydrobenzo[f][12]-annulen-5-yl 4-nitrobenzoate

1-[(2S)-4-cyano-2-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)butyl]-(1R,2S)-2-methylpent-4-enyl acetate

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