1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine
• CAS No.: 77286-66-9
• Molecular Formula: C₂₇H₅₈NO₆P
• Molecular Weight: 523.734
• Hs Code.: 2923200000
• UNII: LZ198HY9OE
• DSSTox Substance ID: DTXSID20922896
• Wikidata: Q27147892
• ChEMBL ID: CHEMBL107514
• Mol file: 77286-66-9.mol

Synonyms:1-O-octadecyl-2-methyl-3-phosphatidylcholine;1-O-octadecyl-2-O-methyl-glycero-phosphocholine;1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine;1-O-octadecyl-2-O-methylglycerophosphocholine;1-octadecyl-2-methoxy-sn-glycero-3-phosphorylcholine;1-octadecyl-2-methoxyglycero-3-phosphorylcholine;1-octadecyl-2-methyl-sn-glycero-3-phosphocholine;1-octadecyl-2-methylglycero-3-phosphocholine;2-methoxy-PAF;edelfosine;edelfosine, (+-)-isomer;edelfosine, (R)-isomer;edelfosine, (S)-isomer;ET-18-O-methyl;ET-18-OCH(3);ET-18-OCH3;ET18-OCH3;ET18-OMe;L-ET-18-OCH3;TLC ELL-12

Chemical Property of 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine

Chemical Property:

• PSA: 86.86000
• LogP: 7.55750
• Storage Temp.: −20°C
• Solubility.: ethanol: 15 mg/mL at 45 °C, soluble
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 27
• Exact Mass: 523.40017557
• Heavy Atom Count: 35
• Complexity: 492

Purity/Quality:

98%,99%, ^*data from raw suppliers

Edelfosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC
• Uses: Edelfosine or 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine might be used:as a non-hydrolysable LysoPC (phospholipid) analog for analyzing its ability to block sexual commitment in Plasmodium falciparumin multilamellar vesicle preparation to study its effect on model membranesin the selection and screening of mutagenized cells, having the ability to inhibit the transport of alkylphosphocholine drugs across the plasma membrane

Technology Process of 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine

There total 52 articles about 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine 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: 90.0%

2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate + 1-O-octadecyl-2-O-methyl-sn-glycerol (83167-59-3) → (+)-Edelfosine (65492-82-2,77286-66-9)

Guidance literature:

2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate; 1-O-octadecyl-2-O-methyl-sn-glycerol; With 1H-tetrazole; In acetonitrile; at 25 ℃; for 0.5h; Inert atmosphere;

With tert.-butylhydroperoxide; In acetonitrile;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; Inert atmosphere;

DOI:10.1039/c9ob02582k

Reference yield: 65.0%

Cholin-p-toluolsulfonsaeureester + 1-O-octadecyl-2-O-methyl-sn-glycerol (83167-59-3) → (+)-Edelfosine (65492-82-2,77286-66-9)

Guidance literature:

With pyridine; triethylamine; trichlorophosphate; In chloroform; Ambient temperature;

DOI:10.1002/hlca.19820650339

Reference yield:

1-octadecyl methanesulfonate (31081-59-1) → (+)-Edelfosine (65492-82-2,77286-66-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / NaH / dimethylformamide / a) 25 deg C, 14 h, b) 40 deg C, 4 h

2: 96 percent / H₂ / 10percent Pd/C / ethanol; hexane / 24 h / 20 °C

3: 1.) NaIO₄, 2.) NaBH₄ / 1.) H₂O, CH₃OH, THF, RT, 24 h, 2.) H₂O, CH₃OH, THF, RT, 1.5 h

4: Et₃N / benzene / 12 h / 20 °C

5: acetonitrile / 30 h / 70 °C

With sodium tetrahydroborate; sodium periodate; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In ethanol; hexane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/0009-3084(93)90082-E

upstream raw materials:

2-(2-Methoxy-3-octadecyloxy-propoxy)-[1,3,2]dioxaphospholane 2-oxide

trimethylamine

Phosphoric acid 2-bromo-ethyl ester 2-methoxy-3-octadecyloxy-propyl ester

2-methoxy-3-octadecyloxy-1-propanol

Refernces

• 1、 -. "D and L etherlipid stereoisomers and liposomes". Page column 11-12. . Retrieved 2008/06/13.
• 2、 Villa,Pallavicini,Villa,Valoti,Ferri,Maderna. "Chiral PAF agonists: Synthesis, theoretical analysis of their stereoelectronic properties and structure activity relationships". . p. 573 - 613. Retrieved 2007/10/02.