Sphingomyelin d18:1-C16:0

Base Information

• Chemical Name: Sphingomyelin d18:1-C16:0
• CAS No.: 536-14-1
• Molecular Formula: C₃₉H₇₉N₂O₆P
• Molecular Weight: 703.04
• DSSTox Substance ID: DTXSID401346510
• Mol file: 536-14-1.mol

Synonyms:Sphingomyelin d18:1-C16:0;383907-87-7;536-14-1;P-SPM;DTXSID401346510;NSC772685;NSC-772685;SM 18:1;2O/16:0

Chemical Property of Sphingomyelin d18:1-C16:0

Chemical Property:

• XLogP3: 12.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 36
• Exact Mass: 702.56757524
• Heavy Atom Count: 48
• Complexity: 796

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(COP(=O)([O-])OCC[N+](C)(C)C)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)NC(COP(=O)([O-])OCC[N+](C)(C)C)C(/C=C/CCCCCCCCCCCCC)O

Technology Process of Sphingomyelin d18:1-C16:0

There total 27 articles about Sphingomyelin d18:1-C16:0 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: 92.0%

(2S,3R,4E)-2-hexadecanoylamino-1-phosphorylcholine-3-(tert-butyldimethylsilyloxy)-octadecene (127028-37-9) → N-palmitoyl-D-erythro-sphingomyelin (536-14-1,4846-15-5,13053-57-1,6254-89-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1016/S0040-4039(00)92367-0

Reference yield: 90.0%

N-palmitoyl-3-O-benzoyl-D-erythro-sphingomyelin → N-palmitoyl-D-erythro-sphingomyelin (536-14-1,4846-15-5,13053-57-1,6254-89-3)

Guidance literature:

With sodium methylate; In methanol; at 22 ℃; for 23h; pH=11.5; Large scale;

Reference yield: 70.0%

2-bromoethyl (2S)-N-(1-oxohexadecyl)amino-(3R)-hydroxy-(4E)-octadecenyl methyl phosphate (875112-70-2) + trimethylamine (75-50-3) → N-palmitoyl-D-erythro-sphingomyelin (536-14-1,4846-15-5,13053-57-1,6254-89-3)

Guidance literature:

In methanol; at 50 ℃; for 5h;

DOI:10.1021/ol062258l

upstream raw materials:

trimethylamine

(2S,3R,4E)-2-hexadecanoylamino-1-phosphorylcholine-3-(tert-butyldimethylsilyloxy)-octadecene

2-bromoethyl (2S)-N-(1-oxohexadecyl)amino-(3R)-hydroxy-(4E)-octadecenyl methyl phosphate

1-(tert-butyldimethylsilyloxy)-(2S)-(N-tert-butyloxycarbonyl)amino-3-oxo-4-pentene

Refernces

• 1、 -. "NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS". Paragraph 0111. . Retrieved 2016/04/19.
• 2、 -. "METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS". Paragraph 00254; 00255. . Retrieved 2014/09/29.