(4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate

Base Information

• Chemical Name: (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate
• CAS No.: 791819-15-3
• Molecular Formula: C₅₂H₉₈O₅Si₃
• Molecular Weight: 887.604
• Mol file: 791819-15-3.mol

Synonyms:(4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate

Chemical Property of (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate

There total 12 articles about (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate 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: 71.0%

Cinnamoyl chloride (102-92-1,17082-09-6) + (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol (791819-14-2) → (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate (791819-15-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/jo049275d

Reference yield:

n-hexadecylaldehyde (629-80-1) → (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate (791819-15-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

1.2: diethyl ether / 1 h / -100 °C

2.1: 93 percent / imidazole / dimethylformamide / 18 h / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / CH₂Cl₂ / 2 h / 20 °C

4.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

4.2: diethyl ether / 1 h / -100 °C

4.3: TBAF / tetrahydrofuran / 1.5 h / 20 °C

5.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: PPh₃ / CH₂Cl₂ / 2 h / 20 °C

7.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

7.2: diethyl ether / 1 h / -100 °C

8.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

9.1: O₃ / CH₂Cl₂ / -78 °C

9.2: PPh₃ / CH₂Cl₂ / 2 h / 20 °C

10.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

10.2: diethyl ether / 1 h / -100 °C

11.1: 71 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; ozone; triethylamine; B-chlorodiisopinocampheylborane; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo049275d

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-yl (E)-3-phenylacrylate (791819-15-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: PPh₃ / CH₂Cl₂ / 2 h / 20 °C

3.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

3.2: diethyl ether / 1 h / -100 °C

4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: PPh₃ / CH₂Cl₂ / 2 h / 20 °C

6.1: (+)-diisopinocampheylboron chloride / diethyl ether / 1 h / cooling

6.2: diethyl ether / 1 h / -100 °C

7.1: 71 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 20 °C

With 2,6-dimethylpyridine; dmap; ozone; triethylamine; B-chlorodiisopinocampheylborane; In diethyl ether; dichloromethane;

DOI:10.1021/jo049275d

upstream raw materials:

Cinnamoyl chloride

(4R,6R,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol

n-hexadecylaldehyde

t-butyldimethylsiyl triflate