329327-15-3

Upstream product

• 14811-92-8 (R)-2,3-dihydroxypropyl stearate 
• 596-38-3 9-phenyl-9H-xanthen-9-ol 
• 112-76-5 Stearoyl chloride 
• 10567-18-7 (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate 

Downstream Products

• 329327-16-4 (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (R)-1-octadecanoyloxymethyl-2-(9-phenyl-9H-xanthen-9-yloxy)-ethyl ester 
• 65914-84-3 1-stearoyl-2-arachidonoyl-sn-glycerol 
• 150577-01-8 2-O-Arachidonoyl-3-O-stearoyl-sn-glycerol 

Relevant academic research and scientific papers

Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers

The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-triphosphate [PtdIns(3,4,5)P3] and its diastereoisomers was discussed. In the first stage, the preparation of the required enantiomeric 1,2-di-O-acylglycerol derivatives was done. The second stage involved the preparation of suitably protected enantiomeric myo-inositol 1-phosphates. The glycerol and inositol building blocks were coupled together and the 3-, 4- and 5-hydroxy functions of the inositol residues in the coupled products were phosphorylated. Finally, the protecting groups were removed to give PtdIns(3,4,5)P3 and its diastereoisomers.

Preparation of 2-O-arachidonoyl-1-O-stearoyl-sn-glycerol and other di-O-acyl glycerol derivatives

R(-)-2,3- and S(+)-1,2-O-Isopropylidene-sn-glycerols (4 and 9) are converted into 2-O-arachidonoyl-1-O-stearoyl and 2-O-arachidonoyl-3-O-stearoyl-sn-glycerols (2 and 3, respectively); glycerol is also converted into its racemic 1,2- and its symmetrical 13-di-O-linoleoyl derivatives (14 and 17, respectively).