N-(octadecanoyl)-sphing-4-enine-1-phosphocholine

Base Information

• Chemical Name: N-(octadecanoyl)-sphing-4-enine-1-phosphocholine
• CAS No.: 58909-84-5
• Molecular Formula: C41H83 N2 O6 P
• Molecular Weight: 731.094
• UNII: 05UG6280NI
• DSSTox Substance ID: DTXSID501313528
• Wikidata: Q27156784
• Metabolomics Workbench ID: 30726
• ChEMBL ID: CHEMBL1609656
• Mol file: 58909-84-5.mol

Synonyms:2,3-(N-steroylsphingosyl)-1-phosphocholine;2,3-SPPC

Chemical Property of N-(octadecanoyl)-sphing-4-enine-1-phosphocholine

Chemical Property:

• PSA: 117.73000
• LogP: 12.01980
• Storage Temp.: −20°C
• XLogP3: 13.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 38
• Exact Mass: 730.59887537
• Heavy Atom Count: 50
• Complexity: 826

Purity/Quality:

97% ^*data from raw suppliers

N-OCTADECANOYL-D-SPHINGOSINE-1-PHOSPHOCHOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Sphingolipids
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(COP(=O)([O-])OCC[N+](C)(C)C)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O

Technology Process of N-(octadecanoyl)-sphing-4-enine-1-phosphocholine

There total 17 articles about N-(octadecanoyl)-sphing-4-enine-1-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: 86.0%

<(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-yl> <2-(trimethylammonio)ethyl> phosphate (127028-38-0) → sphingomyelin (58909-84-5)

Guidance literature:

With ion exchange resin (H⁺; tetrabutyl ammonium fluoride; hydroxide; 1.) THF, 35 deg C;

DOI:10.1016/S0040-4039(00)91820-3

Reference yield:

C57H101N2O6PSi (115523-50-7) → sphingomyelin (58909-84-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 48h; Yield given; Ambient temperature;

Reference yield:

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol (114299-64-8) → sphingomyelin (58909-84-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / PPh₃ / H₂O; pyridine

2: 88 percent / NEt₃ / tetrahydrofuran

3: iPr₂NH*tetrazole / CH₂Cl₂; acetonitrile / 0.5 h

4: tetrazole

5: I₂ / H₂O; pyridine; CH₂Cl₂

6: 33percent HNMe₂ / ethanol / Ambient temperature

7: 86 percent / 1.) tetrabutylammonium fluoride (TBAF); 2.) ion exchange resin (H⁺, OH^-) / 1.) THF, 35 deg C

With 1H-tetrazole; ion exchange resin (H⁺; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; hydroxide; iodine; dimethyl amine; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)91820-3

upstream raw materials:

trimethylamine

C₅₇H₁₀₁N₂O₆PSi

<(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-yl> <2-(trimethylammonio)ethyl> phosphate

(2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol

Downstream raw materials:

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol

Refernces

• 1、 Kratzer, Bernd,Mayer, Thomas G.,Schmidt, Richard R.. "Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol". . p. 6881 - 6884. Retrieved 2007/10/02.
• 2、 Bruzik, Karol S.. "The Synthesis and Absolute Configuration of Thiosphingomyelins". . p. 329 - 331. Retrieved 2007/10/02.