(3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene

Base Information

• Chemical Name: (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene
• CAS No.: 365440-89-7
• Molecular Formula: C₃₀H₃₈O₆
• Molecular Weight: 494.628
• Mol file: 365440-89-7.mol

Synonyms:(3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene

Chemical Property of (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene

There total 5 articles about (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene 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:

methyl 2,3-dimethyl-4-pentenoate (20459-98-7) → (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene (365440-89-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 95 percent / PPh₃ / CH₂Cl₂ / -78 °C

2.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

2.2: B-isopropoxy-4,4,5,5-tetramethyl-1,3-dioxaborolane / tetrahydrofuran; hexane / 1 h / -78 °C

2.3: 60 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -78 °C

3.1: 82 percent / DIBAH / tetrahydrofuran; petroleum ether / 1 h / -78 °C

4.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -88 - -78 °C

4.2: B-methoxy-9-borabicyclononane / tetrahydrofuran; hexane / 1.25 h / -78 °C

4.3: 72 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -88 °C

5.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C

With n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; ozone; In tetrahydrofuran; hexane; dichloromethane; Petroleum ether;

DOI:10.1002/1099-0690(200107)2001:14<2749::aid-ejoc2749>3.0.co;2-t

Reference yield:

(syn/anti)-2,3-Dimethyl-4-pentenoic acid (59793-05-4) → (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene (365440-89-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / p-toluenesulfonic acid monohydrate / 12 h / Heating

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 95 percent / PPh₃ / CH₂Cl₂ / -78 °C

3.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

3.2: B-isopropoxy-4,4,5,5-tetramethyl-1,3-dioxaborolane / tetrahydrofuran; hexane / 1 h / -78 °C

3.3: 60 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -78 °C

4.1: 82 percent / DIBAH / tetrahydrofuran; petroleum ether / 1 h / -78 °C

5.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -88 - -78 °C

5.2: B-methoxy-9-borabicyclononane / tetrahydrofuran; hexane / 1.25 h / -78 °C

5.3: 72 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -88 °C

6.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C

With n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; hexane; dichloromethane; Petroleum ether;

DOI:10.1002/1099-0690(200107)2001:14<2749::aid-ejoc2749>3.0.co;2-t

Reference yield:

(2S,3R)-2,3-Dimethyl-4-oxo-butyric acid methyl ester → (3R,4R,5R,6S,7S,8S)-4,7-bis(p-methoxybenzoyloxy)-3,5,6,8-tetramethyl-1,9-decadiene (365440-89-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: B-isopropoxy-4,4,5,5-tetramethyl-1,3-dioxaborolane / tetrahydrofuran; hexane / 1 h / -78 °C

1.3: 60 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -78 °C

2.1: 82 percent / DIBAH / tetrahydrofuran; petroleum ether / 1 h / -78 °C

3.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -88 - -78 °C

3.2: B-methoxy-9-borabicyclononane / tetrahydrofuran; hexane / 1.25 h / -78 °C

3.3: 72 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 12 h / -88 °C

4.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C

With n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; Petroleum ether;

DOI:10.1002/1099-0690(200107)2001:14<2749::aid-ejoc2749>3.0.co;2-t

upstream raw materials:

methyl 2,3-dimethyl-4-pentenoate

(syn/anti)-2,3-Dimethyl-4-pentenoic acid

Downstream raw materials:

(2R,3S,4R,5S,6R,7S)-3,6-bis(p-methoxybenzoyloxy)-2,4,5,7-tetramethyloctane-1,8-diol