(1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one

Base Information

• Chemical Name: (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one
• CAS No.: 1170990-33-6
• Molecular Formula: C₂₇H₃₆O₂
• Molecular Weight: 392.582

Synonyms:(1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one

Chemical Property of (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one

There total 23 articles about (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one 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: 85.0%

(1R,2Z,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-8-hydroxy-5-hydroxymethyl-9-methyl-4-(1E)-styrylbicyclo-[4.3.0]non-2-ene (1170990-30-3) → (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one (1170990-33-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2009.02.101

Reference yield:

(2E,4S)-4-(tert-butyldimethylsilyloxymethyl)-2-ethylhex-2-en-1-ol (1170989-60-2) → (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one (1170990-33-6)

Guidance literature:

Multi-step reaction with 20 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

1.2: 21 h / 0 - 20 °C

2.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.25 h / -100 - -50 °C / Inert atmosphere

4.2: 0.5 h / -100 - -78 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / Reflux

6.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 9.5 h / 20 °C

7.1: sodium periodate / water; acetone / 0.83 h / 0 - 20 °C

8.1: n-butyllithium / diethyl ether; hexane / 0.67 h / -40 °C / Inert atmosphere

8.2: 1.5 h / -78 °C / Inert atmosphere

9.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 8 h / 50 °C / Inert atmosphere

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / aq. phosphate buffer

11.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide / tetrahydrofuran; water / 53.5 h / 20 °C / Inert atmosphere

12.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C

13.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 132 h / 70 °C / Inert atmosphere

14.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 - 20 °C

14.2: 0 °C / Saturated solution

15.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / Reflux

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 19.5 h / 0 - 50 °C

16.2: 0 °C / Saturated solution

17.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

17.2: 0.67 h / -78 - 20 °C / Inert atmosphere

18.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

18.2: 3 h / -78 - 0 °C / Inert atmosphere

19.1: camphor-10-sulfonic acid / methanol / 133 h / 40 °C

20.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

With manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; camphor-10-sulfonic acid; potassium tert-butylate; potassium phenolate; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 3.1: Swern oxidation / 3.2: Swern oxidation / 9.1: Miyaura vinylboronation / 11.1: Suzuki-Miyaura coupling / 17.1: Swern oxidation / 17.2: Swern oxidation / 18.2: Horner-Wadsworth-Emmons olefination / 20.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2011.04.006

Reference yield:

ethyl (2E,4S)-4-(tert-butyldimethylsilyloxy)methyl-2-ethyl-hex-2-enoate (1170989-57-7) → (1R,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-5-formyl-9-methyl-4-[(1E)-styryl]bicyclo[4.3.0]non-2-en-8-one (1170990-33-6)

Guidance literature:

Multi-step reaction with 21 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

2.2: 21 h / 0 - 20 °C

3.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.25 h / -100 - -50 °C / Inert atmosphere

5.2: 0.5 h / -100 - -78 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / Reflux

7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 9.5 h / 20 °C

8.1: sodium periodate / water; acetone / 0.83 h / 0 - 20 °C

9.1: n-butyllithium / diethyl ether; hexane / 0.67 h / -40 °C / Inert atmosphere

9.2: 1.5 h / -78 °C / Inert atmosphere

10.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 8 h / 50 °C / Inert atmosphere

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / aq. phosphate buffer

12.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide / tetrahydrofuran; water / 53.5 h / 20 °C / Inert atmosphere

13.1: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C

14.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 132 h / 70 °C / Inert atmosphere

15.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 - 20 °C

15.2: 0 °C / Saturated solution

16.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / Reflux

17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 19.5 h / 0 - 50 °C

17.2: 0 °C / Saturated solution

18.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

18.2: 0.67 h / -78 - 20 °C / Inert atmosphere

19.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

19.2: 3 h / -78 - 0 °C / Inert atmosphere

20.1: camphor-10-sulfonic acid / methanol / 133 h / 40 °C

21.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C

With manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; camphor-10-sulfonic acid; potassium tert-butylate; potassium phenolate; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 4.1: Swern oxidation / 4.2: Swern oxidation / 10.1: Miyaura vinylboronation / 12.1: Suzuki-Miyaura coupling / 18.1: Swern oxidation / 18.2: Swern oxidation / 19.2: Horner-Wadsworth-Emmons olefination / 21.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2011.04.006

upstream raw materials:

(1R,2Z,4S,5R,6R,7S,8S,9S)-2,4,5,7-tetraethyl-8-hydroxy-5-hydroxymethyl-9-methyl-4-(1E)-styrylbicyclo-[4.3.0]non-2-ene

ethyl (2E,4S)-4-(tert-butyldimethylsilyloxy)methyl-2-ethyl-hex-2-enoate

(2E,4S)-4-(tert-butyldimethylsilyloxymethyl)-2-ethylhex-2-en-1-ol

(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

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