(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

Base Information

Chemical Name:(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
CAS No.:620987-50-0
Molecular Formula:C₂₇H₂₈N₂O₇
Molecular Weight:492.529
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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: 89.0%

: 620987-48-6
1-[(2S)-4-cyano-2-(6-methoxy-2-prop-2-enylphenylcarbonyloxy)butyl]-(1R,2S)-2-methylpent-4-enyl 4-nitrobenzoate

: 620987-50-0
(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

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; for 3h; Heating;
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

: 620987-50-0
(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

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: bis(tricyclohexylphosphine)benzylidene ruthenium(IV)Cl₂ / CH₂Cl₂ / 3 h / Heating

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; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 7.1: Wittig reaction / 11.1: 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

: 620987-50-0
(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

Guidance literature:: Multi-step reaction with 8 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

4: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

5: 87 percent / hydrido(triphenylphosphine)copper(I) hexamer / benzene; H₂O / 0.75 h / Heating

6: 89 percent / potassium carbonate / methanol / 5 h / 20 °C

7: 48 percent / diethyl azodicarboxylate; triphenylphosphine / toluene / -30 - 20 °C

8: bis(tricyclohexylphosphine)benzylidene ruthenium(IV)Cl₂ / CH₂Cl₂ / 3 h / Heating

With dmap; hydrido(triphenylphosphine)copper(I) hexamer; diisobutylaluminium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; Grubbs catalyst first generation; In methanol; diethyl ether; hexane; dichloromethane; water; toluene; benzene; 3: Wittig reaction / 7: Mitsunobu esterification;
DOI:10.1021/jo050750x