(R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol

Base Information

• Chemical Name: (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol
• CAS No.: 83526-55-0
• Molecular Formula: C₂₈H₅₀O₅S
• Molecular Weight: 498.768
• Mol file: 83526-55-0.mol

Synonyms:(R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol

Chemical Property of (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol

There total 17 articles about (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol 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: 97.0%

1-octadecanol (112-92-5) + (R)-glycidyl tosylate (113826-06-5,6746-81-2) → (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol (83526-55-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jm900091h

Reference yield:

3-O-Octadecyl-1-O-p-toluolsulfonyl-sn-glycerin (83526-54-9) → (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol (83526-55-0)

Guidance literature:

Multi-step reaction with 12 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: 99 percent / pyridine / CHCl₃ / Ambient temperature

8: 81.5 percent / 1N HCl / dioxane / 1 h / Heating

9: t-BuOK / tetrahydrofuran / Ambient temperature

10: dimethylformamide / 80 °C

11: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h

12: pyridine / CH₂Cl₂ / Ambient temperature

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

DOI:10.1002/hlca.19820650339

Reference yield:

(R)-octadecylglycerol (10567-22-3) → (R)-1-O-octadecyl-3-(p-toluenesulfonyl)-glycerol (83526-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / pyridine / Ambient temperature

2: 99 percent / pyridine / CHCl₃ / Ambient temperature

3: 81.5 percent / 1N HCl / dioxane / 1 h / Heating

4: t-BuOK / tetrahydrofuran / Ambient temperature

5: dimethylformamide / 80 °C

6: H₂ / 5percent Pd/C / tetrahydrofuran / 0.25 h

7: pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; hydrogenchloride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19820650339

upstream raw materials:

batyl alcohol

p-toluenesulfonyl chloride

1-octadecanol

(R)-glycidyl tosylate

Downstream raw materials:

2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin

(S)-1-O-octadecyl-2-O-benzyl-glycerol

Lyso-platelet-activating factor (C₁₈)

Phosphoric acid (R)-2-benzyloxy-3-octadecyloxy-propyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester methyl ester

Refernces

• 1、 Andresen, Thomas L.,Jensen, Simon S.,Madsen, Robert,J?rgensen, Kent. "Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue". . p. 7305 - 7314. Retrieved 2007/10/03.
• 2、 Hirth,Barner. "Synthesis of glyceryletherphosphatides, 1st communication. Preparation of 1-0-octadecyl-2-0-acetyl-sn-glyceryl-3-phosphorylcholine ('platelet activating factor'), of its enantiomer and of some analogous compounds". . p. 1059 - 1084. Retrieved 2007/10/02.