2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione

Base Information

• Chemical Name: 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione
• CAS No.: 1329428-68-3
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 1329428-68-3.mol

Synonyms:2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione

Chemical Property of 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione

There total 13 articles about 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione 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:

(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid (1313051-72-7) → 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione (1329428-68-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 0 - 20 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 23 h / 0 °C / Inert atmosphere

6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

With hydrogenchloride; ammonium cerium (IV) nitrate; methanesulfonamide; AD-mix β; potassium tert-butylate; sodium hexamethyldisilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2.2: Wittig reaction / 4.2: Wittig reaction / 5.1: Sharpless dihydroxylation;

DOI:10.1016/j.tet.2011.03.064

Reference yield:

(R)-1,4-dimethoxy-2-(5-methoxypent-4-en-2-yl)-5-methylbenzene (1329428-62-7) → 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione (1329428-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 0 - 20 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 23 h / 0 °C / Inert atmosphere

4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

With hydrogenchloride; ammonium cerium (IV) nitrate; methanesulfonamide; AD-mix β; potassium tert-butylate; In tetrahydrofuran; water; acetonitrile; tert-butyl alcohol; 2.2: Wittig reaction / 3.1: Sharpless dihydroxylation;

DOI:10.1016/j.tet.2011.03.064

Reference yield:

(R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one (1260083-80-4) → 2-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione (1329428-68-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / 3.5 h / 50 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 6 h / 0 - 20 °C / Inert atmosphere

5.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

5.2: 0.5 h / 0 - 20 °C / Inert atmosphere

6.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 23 h / 0 °C / Inert atmosphere

7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; ammonium cerium (IV) nitrate; methanesulfonamide; AD-mix β; potassium tert-butylate; sodium hexamethyldisilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3.2: Wittig reaction / 5.2: Wittig reaction / 6.1: Sharpless dihydroxylation;

DOI:10.1016/j.tet.2011.03.064

upstream raw materials:

(R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one

(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid

(R)-1,4-dimethoxy-2-(5-methoxypent-4-en-2-yl)-5-methylbenzene

(R)-4-(2,5-dimethoxy-4-methylphenyl)pentanal