2-[(2-Acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium

Base Information

• Chemical Name: 2-[(2-Acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium
• CAS No.: 77286-68-1
• Molecular Formula: C₂₆H₅₄NO₇P
• Molecular Weight: 523.691
• Hs Code.: 2923900090
• DSSTox Substance ID: DTXSID10274371,DTXSID20868306
• Mol file: 77286-68-1.mol

Synonyms:rac-Platelet activating factor;77286-68-1;2-[(2-acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium;Paf enantiomer;SCHEMBL12235513;DTXSID10274371;DTXSID20868306;1-O-Palmityl-2-acetyl-rac-glycero-3-phosphocholine, ~99%;7-(Acetyloxy)-4-hydroxy-N,N,N-trimethyl-4-oxo-3,5,9-trioxa-4lambda~5~-phosphapentacosan-1-aminium

Chemical Property of 2-[(2-Acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium

Chemical Property:

• PSA: 101.10000
• LogP: 6.25580
• Storage Temp.: −20°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 524.37161509
• Heavy Atom Count: 35
• Complexity: 554

Purity/Quality:

1-O-PALMITYL-2-ACETYL-RAC-GLYCERO-3-PHOSPHOCHOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(COP(=O)(O)OCC[N+](C)(C)C)OC(=O)C

Technology Process of 2-[(2-Acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium

There total 14 articles about 2-[(2-Acetyloxy-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium 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: 95.0%

acetic anhydride (108-24-7) + 2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate (78119-19-4,17364-21-5) → 3-O-hexadecyl-2-acetyl-sn-glycero-1-phosphocholine (77286-68-1)

Guidance literature:

With pyridine; at 40 ℃; for 8h;

Reference yield:

2-benzyloxy-3-hexadecyloxy-1-propanol (18678-94-9) → 3-O-hexadecyl-2-acetyl-sn-glycero-1-phosphocholine (77286-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) POCl₃, Et₃N, 2.) pyridine / 1.) CHCl₃, 60-65 deg C, 30 min, 2.) CHCl₃, RT, 5 h

2: 99 percent / H₂ / 10percent Pd/C / methanol / 3 h / 1551.4 Torr / Ambient temperature

3: 89 percent / DMAP

With pyridine; dmap; hydrogen; triethylamine; trichlorophosphate; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00379a015

Reference yield:

Rac. 1-O-Hexadecyl-2-O-benzylglycero-3-phosphocholin (18678-98-3) → 3-O-hexadecyl-2-acetyl-sn-glycero-1-phosphocholine (77286-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / H₂ / 10percent Pd/C / methanol / 3 h / 1551.4 Torr / Ambient temperature

2: 89 percent / DMAP

With dmap; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00379a015

upstream raw materials:

acetic anhydride

2-hydroxy-3-(hexadecyloxy)-propyl 2-trimethylammonioethyl phosphate

trimethylamine

3-(hexadecyloxy)-1,2-propanediol

Downstream raw materials:

1-palmityl-sn-glycero-3-phosphocholine

3-O-hexadecyl-2-O-acetyl-sn-glycero-1-phosphocholine

PAF