2-thio PAF

Base Information

• Chemical Name: 2-thio PAF
• CAS No.: 96801-55-7
• Molecular Formula: C₂₆H₅₄NO₆PS
• Molecular Weight: 539.758
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID50557796
• Mol file: 96801-55-7.mol

Synonyms:2-thio PAF;96801-55-7;2-[(2-acetylsulfanyl-3-hexadecoxypropoxy)-hydroxyphosphoryl]oxyethyl-trimethylazanium;1-O-Hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine;DTXSID50557796;7-(Acetylsulfanyl)-4-hydroxy-N,N,N-trimethyl-4-oxo-3,5,9-trioxa-4lambda~5~-phosphapentacosan-1-aminium

Chemical Property of 2-thio PAF

Chemical Property:

• PSA: 120.00000
• LogP: 7.41060
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 540.34877165
• Heavy Atom Count: 35
• Complexity: 559

Purity/Quality:

98%Min ^*data from raw suppliers

2-thio-PAF ≥98% ^*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)SC(=O)C

Technology Process of 2-thio PAF

There total 21 articles about 2-thio PAF 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: 65.0%

2-(1-Hexadecyl-2-thioacetyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane (121358-37-0) + trimethylamine (75-50-3) → 1-O-hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine (96801-55-7)

Guidance literature:

In acetonitrile; at 65 ℃; for 24h;

DOI:10.1055/s-1989-27132

Reference yield: 61.0%

C24H51NO5PS(1-)*Ag(1+) + acetic anhydride (108-24-7) → 1-O-hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine (96801-55-7)

Guidance literature:

With dmap; potassium iodide; In acetonitrile; for 16h;

Reference yield: 47.0%

Thioacetic acid S-{(R)-2-[(2-bromo-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecyloxymethyl-ethyl} ester (112025-92-0) + trimethylamine (75-50-3) → 1-O-hexadecyl-2-deoxy-2-thio-S-acetyl-sn-glyceryl-3-phosphorylcholine (96801-55-7)

Guidance literature:

In chloroform; at 65 ℃; for 14h;

DOI:10.1055/s-1989-27132

upstream raw materials:

Thioacetic acid S-{(R)-2-[(2-bromo-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecyloxymethyl-ethyl} ester

trimethylamine

2-(1-Hexadecyl-2-thioacetyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane

(R)-3-(hexadecyloxy)-1,2-propanediol

Refernces

• 1、 Murata,Ikoma,Achiwa. "New synthesis of 2-thio-PAF and related compounds as substrates of PAF acetylhydrolase and phospholipase A2". . p. 1335 - 1336. Retrieved 2007/10/02.
• 2、 Bhatia, Suresh K.,Hajdu, Joseph. "STEREOSPECIFIC SYNTHESIS OF PAF ANALOGUES. PREPARATION OF 1-HEXADECYL 2-THIOACETYL-2-DEOXYGLYCEROPHOSPHOCHOLINE (2-THIOPAF)". . p. 1729 - 1732. Retrieved 2007/10/02.