Ilmofosine

Base Information

• Chemical Name: Ilmofosine
• CAS No.: 83519-04-4
• Deprecated CAS: 89315-55-9
• Molecular Formula: C₂₆H₅₆NO₅PS
• Molecular Weight: 525.774
• European Community (EC) Number: 635-994-0
• NSC Number: 601679
• UNII: 5ZZK34MC3V
• DSSTox Substance ID: DTXSID2049008
• Nikkaji Number: J424.110J
• Wikidata: Q27263125
• NCI Thesaurus Code: C166877
• ChEMBL ID: CHEMBL28930
• Mol file: 83519-04-4.mol

Synonyms:1-hexadecylmercapto-2-methoxymethyl-3-propylphosphoric acid monocholine ester;1-mercaptohexadecyl-2-methoxymethyl-syn-glycero-3-phosphocholine;BM 41.440;BM-41440;HMMPAM;ilmofosine;ilmofosine, hydroxide inner salt, (+-)-isomer;SH-MM-lysolecithin

Chemical Property of Ilmofosine

Chemical Property:

• Storage Temp.: −20°C
• Solubility.: H2O: soluble10mg/mL
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 26
• Exact Mass: 525.36168206
• Heavy Atom Count: 34
• Complexity: 482

Purity/Quality:

Ilmofosine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCSCC(COC)COP(=O)([O-])OCC[N+](C)(C)C
• Uses: Ilmofosine is a PKC inhibitor with efficacy against a variety of cancer cell lines.

Technology Process of Ilmofosine

There total 3 articles about Ilmofosine 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:

3-hexadecylthio-2-methylene-1-propanol (157049-10-0) → Ilmofosine (83519-04-4,89315-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran

2: 1.) borane*dimethyl sulfide, sodium perborate, 2.) POCl₃, triethylamine, 3.) pyridine / 2.) CHCl₃, 3.) CHCl₃, -20 deg C

With pyridine; sodium perborate; dimethylsulfide borane complex; sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)77004-3

Reference yield:

ethyl α-(hexadecylthiomethyl)acrylate (157049-09-7) → Ilmofosine (83519-04-4,89315-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / diisobutylaluminum hydride / tetrahydrofuran

2: NaH / tetrahydrofuran

3: 1.) borane*dimethyl sulfide, sodium perborate, 2.) POCl₃, triethylamine, 3.) pyridine / 2.) CHCl₃, 3.) CHCl₃, -20 deg C

With pyridine; sodium perborate; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)77004-3

Reference yield:

choline tosylate (55357-38-5) + 1-(2-Methoxymethyl-allylsulfanyl)-hexadecane → Ilmofosine (83519-04-4,89315-55-9)

Guidance literature:

With pyridine; sodium perborate; dimethylsulfide borane complex; triethylamine; trichlorophosphate; Yield given. Multistep reaction; 2.) CHCl₃, 3.) CHCl₃, -20 deg C;

DOI:10.1016/S0040-4039(00)77004-3

upstream raw materials:

choline tosylate

3-hexadecylthio-2-methylene-1-propanol

ethyl α-(hexadecylthiomethyl)acrylate

Refernces