(4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone

Base Information

• Chemical Name: (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone
• CAS No.: 501369-20-6
• Molecular Formula: C₂₀H₂₅BrO₄
• Molecular Weight: 409.32

Synonyms:(4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone

Chemical Property of (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone

There total 14 articles about (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone 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%

(4S,5R)-2-bromo-3-methoxymethoxymethyl-4,5-dimethyl-4-vinylcyclohex-2-enone (501369-33-1) + 2-(3,4-dimethoxybenzyloxy)-3-nitropyridine (464896-41-1) → (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone (501369-20-6)

Guidance literature:

(4S,5R)-2-bromo-3-methoxymethoxymethyl-4,5-dimethyl-4-vinylcyclohex-2-enone; With n-butanethiol; magnesium bromide ethyl etherate; In diethyl ether; at 20 ℃; for 15h;

2-(3,4-dimethoxybenzyloxy)-3-nitropyridine; With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 18h; Further stages.;

DOI:10.1021/ja0296531

Reference yield:

pulegone (89-82-7,90449-51-7) → (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone (501369-20-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 70 percent / LDA; LiCl

2.1: 75 percent / KOH / Heating

3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

5.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

5.2: diethyl ether; petroleum ether / 1 h / -78 °C

6.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

7.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

7.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

7.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

8.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

9.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

10.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

11.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

12.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

13.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

14.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

14.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; lithium diisopropyl amide; chloro-trimethyl-silane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether;

DOI:10.1021/ja0296531

Reference yield:

(2RS,3R)-2,3-dimethylcyclohexanone (234078-11-6) → (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone (501369-20-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

1.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

2.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

3.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

3.2: diethyl ether; petroleum ether / 1 h / -78 °C

4.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

5.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

5.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

5.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

6.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

7.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

8.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

9.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

10.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

11.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

12.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

12.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; chloro-trimethyl-silane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether;

DOI:10.1021/ja0296531

upstream raw materials:

(4S,5R)-2-bromo-3-methoxymethoxymethyl-4,5-dimethyl-4-vinylcyclohex-2-enone

2-(3,4-dimethoxybenzyloxy)-3-nitropyridine

(3R)-6-bromo-2,3-dimethylcyclohexanone

pulegone

Downstream raw materials:

(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-3-triethylsilanyloxy-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

[(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone

[(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2R,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanol

(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 501369-20-6 (4S,5R)-2-bromo-3-(3,4-dimethoxybenzyloxymethyl)-4,5-dimethyl-4-vinyl-cyclohex-2-enone

Send

Send

Metric Ton KG G Pound L ML

Send

Send