(5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol

Base Information

• Chemical Name: (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol
• CAS No.: 126580-61-8
• Molecular Formula: C₃₁H₄₄OSi
• Molecular Weight: 460.775
• Mol file: 126580-61-8.mol

Synonyms:(5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol

Chemical Property of (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol

There total 6 articles about (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol 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:

Methanesulfonic acid (2S,5S)-1-[2-(tert-butyl-diphenyl-silanyloxymethyl)-allyl]-2-isopropyl-5-methyl-hept-6-enyl ester → (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol (126580-61-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 80 - 90 ℃; for 45h; Yield given;

DOI:10.1021/jo00299a040

Reference yield:

(2S,5R)-2-isopropyl-5-methylhept-6-en-1-ol (126580-55-0) → (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol (126580-61-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) oxalyl chloride, dimethyl sulfoxide; 2) triethylamine / 1) CH₂Cl₂, - 78 deg C, 15 min; 2) 45 min at -78 deg C, then within 1 h to room temp.

2: 79 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

3: triethylamine / CH₂Cl₂ / 1 h / -6 °C

4: potassium tert-butoxide / 2-methyl-propan-2-ol / 45 h / 80 - 90 °C

With oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00299a040

Reference yield:

(2S,5R)-2-isopropyl-5-methylhept-6-enal (126580-59-4) → (5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-3,9-decadien-1-ol (126580-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

2: triethylamine / CH₂Cl₂ / 1 h / -6 °C

3: potassium tert-butoxide / 2-methyl-propan-2-ol / 45 h / 80 - 90 °C

With boron trifluoride diethyl etherate; potassium tert-butylate; triethylamine; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00299a040

upstream raw materials:

(2S,5R)-2-isopropyl-5-methylhept-6-en-1-ol

(2S,5R)-2-isopropyl-5-methylhept-6-enal

(2S,5R)-2-isopropyl-5-methylhept-6-enoic acid

(5S,8R)-1-O-(tert-butyldiphenylsilyl)-5-isopropyl-8-methyl-2-methylene-9-decene-1,4-diol