3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal

Base Information

• Chemical Name: 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal
• CAS No.: 96854-58-9
• Molecular Formula: C₃₂H₄₆O₃S₂
• Molecular Weight: 542.847
• Mol file: 96854-58-9.mol

Synonyms:

Chemical Property of 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal

There total 12 articles about 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal 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: 50.5%

3,11-di(benzyl)oxy-1-hydroxy-9-oxohexadecane-9-ethylenedithioacetal (96854-57-8) → 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal (96854-58-9)

Guidance literature:

With chromium(VI) oxide; In pyridine; for 18h; Ambient temperature;

DOI:10.1080/00021369.1985.10866672

Reference yield:

methyl (+/-)-8-bromo-3-oxooctanoate (64670-06-0) → 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal (96854-58-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NaBH₄ / methanol / 1 h / 0 °C

2: 1 M DIBAL / tetrahydrofuran; hexane / 1 h / -20 °C

3: p-TsOH / dioxane / 1 h / 20 °C

4: 1.) Mg, I₂ / 1. ) THF, 20 min, reflux; 2.) THF, -10 deg C to RT, 45 min

5: 69.6 percent / pyridinium dichromate / dimethylformamide / 18 h / Ambient temperature

6: 62.8 percent / BF₃*etherate / CH₂Cl₂ / 18 h / Ambient temperature

7: 96.9 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / Ambient temperature

8: 60 percent NaH, Bu₄NI / tetrahydrofuran / RT, 1.5 h; 2 d

9: p-TsOH / methanol; CHCl₃ / 2.5 h / 20 °C

10: 50.5 percent / CrO₃ / pyridine / 18 h / Ambient temperature

With chromium(VI) oxide; dmap; sodium tetrahydroborate; dipyridinium dichromate; boron trifluoride diethyl etherate; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1080/00021369.1985.10866672

Reference yield:

8-Bromo-octane-1,3-diol (96854-42-1) → 3,11-di(benzyl)oxy-9-oxohexadecanal-9-ethylenedithioacetal (96854-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH / dioxane / 1 h / 20 °C

2: 1.) Mg, I₂ / 1. ) THF, 20 min, reflux; 2.) THF, -10 deg C to RT, 45 min

3: 69.6 percent / pyridinium dichromate / dimethylformamide / 18 h / Ambient temperature

4: 62.8 percent / BF₃*etherate / CH₂Cl₂ / 18 h / Ambient temperature

5: 96.9 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / Ambient temperature

6: 60 percent NaH, Bu₄NI / tetrahydrofuran / RT, 1.5 h; 2 d

7: p-TsOH / methanol; CHCl₃ / 2.5 h / 20 °C

8: 50.5 percent / CrO₃ / pyridine / 18 h / Ambient temperature

With chromium(VI) oxide; dmap; dipyridinium dichromate; boron trifluoride diethyl etherate; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1080/00021369.1985.10866672

upstream raw materials:

3,11-di(benzyl)oxy-1-hydroxy-9-oxohexadecane-9-ethylenedithioacetal

methyl (+/-)-8-bromo-3-oxooctanoate

8-Bromo-octane-1,3-diol

(+/-)-8-bromo-1,3-dihydroxyoctane-1,3-isopropylideneacetal

Downstream raw materials:

C₆₈H₈₆O₄S₄

8-(2-{2-Benzyloxy-7-[2-(2-benzyloxy-heptyl)-[1,3]dithiolan-2-yl]-heptyl}-[1,3]dithiolan-2-yl)-1-trityloxy-octan-3-ol

3-Benzyloxy-8-(2-{2-benzyloxy-7-[2-(2-benzyloxy-heptyl)-[1,3]dithiolan-2-yl]-heptyl}-[1,3]dithiolan-2-yl)-octanal

3-Benzyloxy-8-(2-{2-benzyloxy-7-[2-(2-benzyloxy-heptyl)-[1,3]dithiolan-2-yl]-heptyl}-[1,3]dithiolan-2-yl)-octan-1-ol