3-O-Acetyl-1-O-octadecyl-sn-glycerin

Base Information

• Chemical Name: 3-O-Acetyl-1-O-octadecyl-sn-glycerin
• CAS No.: 83526-72-1
• Molecular Formula: C₂₃H₄₆O₄
• Molecular Weight: 386.616
• Mol file: 83526-72-1.mol

Synonyms:

Chemical Property of 3-O-Acetyl-1-O-octadecyl-sn-glycerin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-Acetyl-1-O-octadecyl-sn-glycerin

There total 25 articles about 3-O-Acetyl-1-O-octadecyl-sn-glycerin 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: 91.0%

vinyl acetate (108-05-4,9003-20-7) + batyl alcohol (6129-13-1) → 3-O-Acetyl-1-O-octadecyl-sn-glycerin (83526-72-1,85712-13-6)

Guidance literature:

With Candida antarctica lipase B; In dichloromethane; at 20 ℃; for 3h; regioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2011.01.032

Reference yield:

n-octadecyl p-toluenesulfonate (3386-32-1) → 3-O-Acetyl-1-O-octadecyl-sn-glycerin (83526-72-1,85712-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH / tetrahydrofuran

2: aq. p-TsOH / tetrahydrofuran / Heating

3: lipase AK (Amano) / CHCl₃ / 72 h / 22 °C

With lipase AK (Amano); sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; chloroform; 1: Substitution / 2: deprotection / 3: Acylation;

DOI:10.1016/S0957-4166(99)00397-3

Reference yield:

3-O-Octadecyl-1-O-p-toluolsulfonyl-sn-glycerin (83526-54-9) → 3-O-Acetyl-1-O-octadecyl-sn-glycerin (83526-72-1,85712-13-6)

Guidance literature:

Multi-step reaction with 10 steps

1: toluene / 1 h / 80 °C

2: pyridine / CHCl₃ / Ambient temperature

3: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature

4: phosphorus oxychloride, Et₃N, pyridine / CHCl₃ / Ambient temperature

5: 66 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

6: 81 percent / pyridine / Ambient temperature

7: NaH / dimethylformamide / 80 °C

8: 1N HCl / dioxane / 90 °C

9: pyridine / CHCl₃ / Ambient temperature

10: H₂ / 5percent Pd/C / tetrahydrofuran / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium hydride; triethylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.19820650339

upstream raw materials:

1-O-octadecyl-2-O-acetyl-Sn glycerol

1-O-Acetyl-2-O-benzyl-3-O-octadecyl-sn-glycerin

vinyl acetate

batyl alcohol

Refernces

• 1、 Magnusson, Carlos D.,Gudmundsdottir, Anna V.,Haraldsson, Gudmundur G.. "Chemoenzymatic synthesis of a focused library of enantiopure structured 1-O-alkyl-2,3-diacyl-sn-glycerol type ether lipids". supporting information; experimental part. p. 1821 - 1836. Retrieved 2011/04/17.
• 2、 Haraldsson, Gudmundur G.,Thordarson, Pall,Halldorsson, Arnar,Kristinsson, Bjorn. "Kinetic resolution of 1-O-alkylglycerols by lipase". . p. 3671 - 3674. Retrieved 2007/10/03.