(S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester

Base Information

• Chemical Name: (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
• CAS No.: 500002-03-9
• Molecular Formula: C₂₅H₄₀O₅
• Molecular Weight: 420.59
• Mol file: 500002-03-9.mol

Synonyms:(S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester

Chemical Property of (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester

There total 16 articles about (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 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: 77.0%

ethyl cyanoformate (623-49-4) + (S)-4-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-4-methyl-cyclohex-2-enone (499797-50-1) → (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester (500002-03-9)

Guidance literature:

(S)-4-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-4-methyl-cyclohex-2-enone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

ethyl cyanoformate; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Further stages.;

DOI:10.1021/ol026820t

Reference yield:

(R)-7-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-5-methyl-heptan-2-ol (499797-48-7) → (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester (500002-03-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

4.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

5.1: 19 g / KOH / methanol / 5 h

6.1: 98 percent / Bu₄NF / tetrahydrofuran / 24 h / 25 °C

7.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

7.2: HMPA / tetrahydrofuran; various solvent(s) / 24 h

7.3: Bu₃SnH; AIBN / toluene / 8 h / 100 °C

8.1: OsO₄; NMO / tetrahydrofuran; H₂O / 24 h / pH 7

9.1: 0.86 g / p-toluenesulfonic acid / dimethylformamide / 1 h

10.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 77 percent / HMPA / tetrahydrofuran; various solvent(s) / 2 h / -78 - 20 °C

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/ol026820t

Reference yield:

(-)-Verbenone (80-57-9,1196-01-6) → (S)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester (500002-03-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Mg; I₂ / tetrahydrofuran / 0.5 h

1.2: 80 percent / CuI / tetrahydrofuran / -50 - 20 °C

2.1: LiAlH₄ / diethyl ether / 0.25 h

3.1: 4.9 g / imidazole / dimethylformamide / 2.5 h

4.1: O₃ / CH₂Cl₂ / 4 h / -78 °C

5.1: 30.5 g / diethyl ether; tetrahydrofuran / 2 h / 0 °C

6.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

8.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

9.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

10.1: 19 g / KOH / methanol / 5 h

11.1: 98 percent / Bu₄NF / tetrahydrofuran / 24 h / 25 °C

12.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

12.2: HMPA / tetrahydrofuran; various solvent(s) / 24 h

12.3: Bu₃SnH; AIBN / toluene / 8 h / 100 °C

13.1: OsO₄; NMO / tetrahydrofuran; H₂O / 24 h / pH 7

14.1: 0.86 g / p-toluenesulfonic acid / dimethylformamide / 1 h

15.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

15.2: 77 percent / HMPA / tetrahydrofuran; various solvent(s) / 2 h / -78 - 20 °C

With pyridine; 1H-imidazole; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; iodine; sodium hydride; toluene-4-sulfonic acid; ozone; magnesium; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 5.1: Grignard reaction;

DOI:10.1021/ol026820t

upstream raw materials:

ethyl cyanoformate

(S)-4-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-4-methyl-cyclohex-2-enone

(R)-7-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-5-methyl-heptan-2-ol

(-)-Verbenone

Downstream raw materials:

(R)-5-[2-((5S,6R)-6-Isopropyl-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxol-5-yl)-ethyl]-5-methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester