C₄₀H₆₄O₂Si₂

Base Information

• Chemical Name: C₄₀H₆₄O₂Si₂
• CAS No.: 470467-04-0
• Molecular Formula: C₄₀H₆₄O₂Si₂
• Molecular Weight: 633.118
• Mol file: 470467-04-0.mol

Synonyms:C₄₀H₆₄O₂Si₂

Chemical Property of C₄₀H₆₄O₂Si₂

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₀H₆₄O₂Si₂

There total 14 articles about C₄₀H₆₄O₂Si₂ 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: 87.0%

n-propyltriphenylphosphonium bromide (6228-47-3) + {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde (470467-03-9) → C40H64O2Si2 (470467-04-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1021/jo0348571

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → C40H64O2Si2 (470467-04-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 88 percent / CuCN; t-BuMgCl / tetrahydrofuran / 2 h / -18 °C

2: 93 percent / PPh₃; DEAD / toluene / 2 h / -78 - -60 °C

3: 91 percent / MeLi / diethyl ether / 0.67 h / 0 °C

4: 85 percent / Hg(OAc)3 / benzene / 61 h / 170 °C

5: 93 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

6: 88 percent / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 13 h / 20 °C

7: 84 percent / DBU / tetrahydrofuran / 6 h / Heating

8: LiOH*H₂O; H₂O / tetrahydrofuran; methanol / 1 h / 20 °C

9: diethyl ether / 0.5 h / 0 °C

10: 398 mg / imidazole / dimethylformamide / 1 h / 20 °C

11: 86 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

12: 87 percent / NaN(TMS)2 / tetrahydrofuran; dimethylformamide / 1 h / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; lithium hydroxide; Hg(OAc)3; sulfuric acid; tert-butylmagnesium chloride; water; methyllithium; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 2: Mitsunobu reaction / 4: Claisen rearrangement / 5: Jones oxidation / 12: Wittig reaction;

DOI:10.1021/jo0348571

Reference yield:

(4S,1R)-4-[8-{(tert-butyldiphenylsilyl)oxy}octyl]-2-cyclopenten-1-ol (470466-99-0) → C40H64O2Si2 (470467-04-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / Hg(OAc)3 / benzene / 61 h / 170 °C

2: 93 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

3: 88 percent / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 13 h / 20 °C

4: 84 percent / DBU / tetrahydrofuran / 6 h / Heating

5: LiOH*H₂O; H₂O / tetrahydrofuran; methanol / 1 h / 20 °C

6: diethyl ether / 0.5 h / 0 °C

7: 398 mg / imidazole / dimethylformamide / 1 h / 20 °C

8: 86 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9: 87 percent / NaN(TMS)2 / tetrahydrofuran; dimethylformamide / 1 h / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; lithium hydroxide; Hg(OAc)3; sulfuric acid; water; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1: Claisen rearrangement / 2: Jones oxidation / 9: Wittig reaction;

DOI:10.1021/jo0348571

upstream raw materials:

n-propyltriphenylphosphonium bromide

{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

triethylsilyl chloride

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

Downstream raw materials:

4-oxo-5α-(2Z)-pentenyl-2-cyclopentene-1α-octanoic acid

13-epi-12-oxo-phytodienoic acid

Refernces

• 1、 Ainai, Takayuki,Matsuumi, Michitaka,Kobayashi, Yuichi. "Efficient total synthesis of 12-oxo-PDA and OPC-8:0". . p. 7825 - 7832. Retrieved 2007/10/03.