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

Base Information

Chemical Name:(4E)-(1R,3R)-1-((1S)-1-methylbut-3-enyl)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl 4-nitrobenzoate
CAS No.:620987-46-4
Molecular Formula:C₂₉H₃₀N₂O₇
Molecular Weight:518.566
Hs Code.:

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

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

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

There total 7 articles about (4E)-(1R,3R)-1-((1S)-1-methylbut-3-enyl)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl 4-nitrobenzoate 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: 74.0%

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

: 62-23-7
4-nitro-benzoic acid

: 620987-46-4
(4E)-(1R,3R)-1-((1S)-1-methylbut-3-enyl)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl 4-nitrobenzoate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at -30 - 20 ℃; for 24h;
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

: 620987-46-4
(4E)-(1R,3R)-1-((1S)-1-methylbut-3-enyl)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl 4-nitrobenzoate

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: 75 percent / toluene / 2 h / 80 °C

8.1: 74 percent / diethyl azodicarboxylate; triphenylphosphine / toluene / -30 - 20 °C

With dmap; carbon tetrabromide; methyllithium; copper(l) cyanide; diisobutylaluminium hydride; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 7.1: Wittig reaction / 8.1: Mitsunobu esterification;
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

: 620987-46-4
(4E)-(1R,3R)-1-((1S)-1-methylbut-3-enyl)-5-cyano-3-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)pent-4-enyl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 4 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: 75 percent / toluene / 2 h / 80 °C

4: 74 percent / diethyl azodicarboxylate; triphenylphosphine / toluene / -30 - 20 °C

With dmap; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; hexane; dichloromethane; toluene; 3: Wittig reaction / 4: Mitsunobu esterification;
DOI:10.1021/jo050750x