1-O-OCTADECYL-2-O-METHYL-RAC-GLYCEROL

Base Information

• Chemical Name: 1-O-OCTADECYL-2-O-METHYL-RAC-GLYCEROL
• CAS No.: 84337-43-9
• Molecular Formula: C22H46O3
• Molecular Weight: 358.5988
• Mol file: 84337-43-9.mol

Synonyms:rac-glycero-1-octadecylether-2-methylether;2-methoxy-3-octadecyloxypropanol;rac-1-O-octadecyl-2-O-methylglycerol;2-O-methyl-1-O-octadecylglycero-3-phosphate;2-methoxy-3-octadecyloxy-1-propanol;1-O-octadecyl-2-O-methyl-rac-glycerol;2-O-Methyl-1-O-octadecyl-rac-glycerin;

Chemical Property of 1-O-OCTADECYL-2-O-METHYL-RAC-GLYCEROL

Chemical Property:

• Vapor Pressure: 2.71E-10mmHg at 25°C
• Boiling Point: 457.5°Cat760mmHg
• Flash Point: 230.5°C
• PSA: 38.69000
• Density: 0.891g/cm³
• LogP: 6.27180

Purity/Quality:

99% ^*data from raw suppliers

1-O-Octadecyl-2-O-methyl-rac-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-O-Octadecyl-2-O-methyl-rac-glycerol is used to prepare Edelfosine, a rapid inducer of apoptosis in human leukemic cells. Edelfosine has been considered as a promising drug in cancer treatment. It is also used to prepare phospholipids containing nitrogen homologs with antitumor activities.

Technology Process of 1-O-OCTADECYL-2-O-METHYL-RAC-GLYCEROL

There total 11 articles about 1-O-OCTADECYL-2-O-METHYL-RAC-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: 100.0%

1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol (90940-90-2) → 2-methoxy-3-octadecyloxy-1-propanol (84337-43-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 45 ℃;

DOI:10.1007/BF00766461

Reference yield: 81.0%

2-methylglycerol (761-06-8) + Octadecylsulfonsaeuremethylester (13538-48-2) → 2-methoxy-3-octadecyloxy-1-propanol (84337-43-9)

Guidance literature:

With potassium tert-butylate; In tert-Amyl alcohol; at 90 ℃;

Reference yield:

1-Bromooctadecane (112-89-0) → 2-methoxy-3-octadecyloxy-1-propanol (84337-43-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaNH₂ / toluene / Heating

2: NaNH₂

3: hydrogen / 10percent Pd/C

With hydrogen; sodium amide; palladium on activated charcoal; In toluene;

DOI:10.1021/jm00160a041

upstream raw materials:

1-O-octadecyl-2-O-methyl-3-O-trityl-rac-glycerol

1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol

2-methylglycerol

1-Bromooctadecane

Downstream raw materials:

Edelfosine

Refernces

• 1、 Stekar, Jurij,Noessner, Gerhard,Kutscher, Bernhard,Engel, Juergen,Hilgard, Peter. "Synthese sowie Antitumorwirksamkeit und Vertraeglichkeit im Tierexperiment von elementhomologen Phospholipiden". . p. 195 - 197. Retrieved 2007/10/02.
• 2、 Alunni-Bistocchi,Orvietani,Ricci,Binaglia,Orlando,Orlando. "Synthesis of 1-O-alkyl-2-O-methyl-glycerophospholipids with potential antitumor activity". . p. 499 - 509. Retrieved 2007/10/02.