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

Base Information

Chemical Name:1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate
CAS No.:865622-40-8
Molecular Formula:C₂₂H₂₇NO₄
Molecular Weight:369.461
Hs Code.:

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

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

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

There total 7 articles about 1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 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: 75.0%

: 16640-68-9
cyanomethylene triphenylphosphorane

: 865622-39-5
5-((1S)-1-methylbut-3-enyl)-(3R,5S)-2-hydroxy-oxolan-3-yl 6-methoxy-2-prop-2-enylbenzoate

: 865622-40-8
1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate

: 620987-45-3
1-((1E)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate

Guidance literature:: In toluene; at 80 ℃; for 2h;
DOI:10.1021/jo050750x

Reference yield:

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

: 865622-40-8
1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate

Guidance literature:: Multi-step reaction with 7 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

With dmap; carbon tetrabromide; methyllithium; copper(l) cyanide; diisobutylaluminium hydride; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 7.1: Wittig reaction;
DOI:10.1021/jo050750x

Reference yield:

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

: 865622-40-8
1-((1Z)-2-cyanovinyl)-(1R,3S,4S)-3-hydroxy-4-methylhept-6-enyl 6-methoxy-2-prop-2-enylbenzoate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 21 percent / toluene / 2 h / 80 °C

With dmap; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane; toluene; 3: Wittig reaction;
DOI:10.1021/jo050750x