1-OLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOETHANOLAMINE synthesis
- Product Name:1-OLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOETHANOLAMINE
- CAS Number:89576-29-4
- Molecular formula:C23H46NO7P
- Molecular Weight:479.59
![9-Octadecenoic acid (9Z)-, (2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxypropyl ester](/CAS/20210305/GIF/1609563-03-2.gif)
![Ethanol, 2-[[(4-methoxyphenyl)diphenylmethyl]amino]-](/CAS/20210111/GIF/113019-11-7.gif)
Yield:89576-29-4 54%
Reaction Conditions:
Stage #1: 2-O-tert-butyldimethylsilanyl-1-O-cis-octadec-9-enoyl-sn-glycerolwith pyridine;triethylamine;trichlorophosphate in dichloromethane at 0; for 1 h;
Stage #2: 2-(((4-methoxyphenyl)diphenylmethyl)amino)ethanol in dichloromethane; for 1 h;Further stages;
Steps:
5 4.1.10. General procedure for the synthesis of compounds 5-9
General procedure: To a solution of the POCl3 (1.05 equiv) in DCM was added TEA (20 equiv) and pyridine (1 equiv) dropwise at 0 °C. After 0.5 h, alcohol (15a-15e, 1 equiv) in DCM was added dropwise. After 1 h, N-(monomethoxytrityl)-ethanolamine (2.5 equiv) in DCM was added dropwise and the mixture was stirred 1 h before H2O (0.5 mL) was added. After another 1 h stirring, the mixture was treated with HF-pyridine (2 equiv) and stirred overnight. The resulting mixture was dissolved with DCM and washed with H2O. The organic layer was concentrated, and the residue was purified by flash chromatography on silica gel (CHCl3/MeOH/H2O 70:10:1) to afford the compounds (5-9) as white solid.
References:
Ni, Guanghui;Li, Zhiyuan;Liang, Kangjiang;Wu, Ting;De Libero, Gennaro;Xia, Chengfeng [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 11,p. 2966 - 2973]
![9-Octadecenoic acid (9Z)-, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester](/CAS/20210305/GIF/150447-02-2.gif)
150447-02-2
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