1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether

Base Information

• Chemical Name: 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether
• CAS No.: 96854-55-6
• Molecular Formula: C₃₇H₅₀O₃S₂
• Molecular Weight: 606.934
• Mol file: 96854-55-6.mol

Synonyms:1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether

Chemical Property of 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether

There total 9 articles about 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether 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: 96.9%

trityl chloride (76-83-5) + 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal (96854-54-5) → 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether (96854-55-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1080/00021369.1985.10866672

Reference yield:

methyl (+/-)-8-bromo-3-oxooctanoate (64670-06-0) → 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether (96854-55-6)

Guidance literature:

Multi-step reaction with 7 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

With dmap; sodium tetrahydroborate; dipyridinium dichromate; boron trifluoride diethyl etherate; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00021369.1985.10866672

Reference yield:

8-Bromo-octane-1,3-diol (96854-42-1) → 1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal-1-trityl ether (96854-55-6)

Guidance literature:

Multi-step reaction with 5 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

With dmap; dipyridinium dichromate; boron trifluoride diethyl etherate; iodine; toluene-4-sulfonic acid; magnesium; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/00021369.1985.10866672

upstream raw materials:

trityl chloride

1,3,11-trihydroxy-9-oxohexadecane-9-ethylenedithioacetal

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

8-Bromo-octane-1,3-diol

Downstream raw materials:

2-(2-Benzyloxy-heptyl)-2-(6-benzyloxy-8-trityloxy-octyl)-[1,3]dithiolane

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

(+/-)-PM-toxin B

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