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

Base Information

• Chemical Name: (1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate
• CAS No.: 865622-52-2
• Molecular Formula: C₂₂H₂₉NO₄
• Molecular Weight: 371.477
• Mol file: 865622-52-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate 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: 94.0%

1-[(2S)-4-cyano-2-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)butyl]-(1R,2S)-2-methylpent-4-enyl 4-nitrobenzoate (620987-48-6) → (1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate (865622-52-2)

Guidance literature:

With potassium carbonate; In methanol; 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) → (1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate (865622-52-2)

Guidance literature:

Multi-step reaction with 9 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

6: 87 percent / hydrido(triphenylphosphine)copper(I) hexamer / benzene; H₂O / 0.75 h / Heating

7: 89 percent / potassium carbonate / methanol / 5 h / 20 °C

8: 48 percent / diethyl azodicarboxylate; triphenylphosphine / toluene / -30 - 20 °C

9: 94 percent / potassium carbonate / methanol / 3 h / 20 °C

With dmap; hydrido(triphenylphosphine)copper(I) hexamer; diisobutylaluminium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In methanol; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 4: Wittig reaction / 8: Mitsunobu esterification;

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) → (1S,3R,4S)-1-(2-cyanoethyl)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-(prop-2-enyl)benzoate (865622-52-2)

Guidance literature:

Multi-step reaction with 12 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

9.1: 87 percent / hydrido(triphenylphosphine)copper(I) hexamer / benzene; H₂O / 0.75 h / Heating

10.1: 89 percent / potassium carbonate / methanol / 5 h / 20 °C

11.1: 48 percent / diethyl azodicarboxylate; triphenylphosphine / toluene / -30 - 20 °C

12.1: 94 percent / potassium carbonate / methanol / 3 h / 20 °C

With dmap; carbon tetrabromide; hydrido(triphenylphosphine)copper(I) hexamer; methyllithium; copper(l) cyanide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 7.1: Wittig reaction / 11.1: Mitsunobu esterification;

DOI:10.1021/jo050750x

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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

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