(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

Base Information

Chemical Name:(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide
CAS No.:1303528-22-4
Molecular Formula:C₂₇H₄₂ClNO₄
Molecular Weight:480.088
Hs Code.:

Synonyms:(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

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Chemical Property of (4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

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Technology Process of (4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

There total 9 articles about (4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide 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: 56.0%

: 1303528-07-5
(4R)-4-allyloxy-2-dihydroxyboryl-2-cyclohexen-1-one

: 1303528-04-2
(4E,7S)-N-[(Z)-3-chloro-2-iodoprop-2-ene]-7-methoxytetradec-4-enamide

: 1303528-22-4
(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

Guidance literature:: With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate; In toluene; at 20 ℃; for 30h; Inert atmosphere;
DOI:10.1021/jo2003852

Reference yield:

: (7R,8R)-1,4-dioxaspiro[4.5]decane-7,8-diol

: 1303528-22-4
(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 24 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 0 °C

3.1: bromine; triethylamine / dichloromethane / 0.08 h / 0 °C

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

5.2: 0 - 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

7.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate / toluene / 30 h / 20 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1H-imidazole; hydrogenchloride; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; bromine; palladium diacetate; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: Suzuki cross-coupling;
DOI:10.1021/jo2003852

Reference yield:

: 1303528-18-8
(8R)-6-bromo-8-trimethylsilyloxy-spiro-[4.5]dec-6-ene

: 1303528-22-4
(4E,7S)-N-[(2Z)-((5R)-5-allyloxy-2-oxocyclohex-1-enyl)-2-chloromethyleneethyl]-7-methoxytetradec-4-enamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanol; potassium carbonate / 2 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

2.2: 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate / toluene / 30 h / 20 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; methanol; n-butyllithium; palladium diacetate; sodium hydride; potassium carbonate; caesium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; 4.1: Suzuki cross-coupling;
DOI:10.1021/jo2003852