595605-50-8

Upstream product

• 106-95-6 allyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 18657-14-2 (4R)-2,2-dimethyl-4-{[(prop-2-en-1-yl)oxy]methyl}-1,3-dioxolane 

Downstream Products

• 595605-51-9 (R)-(+)-1-allyl-3-tert-butyldiphenylsilyl-2-(2-trimethylsilanylethoxymethyl)glycerol 
• 595605-52-0 (R)-(+)-3-tert-butyldiphenylsilyl-1-O-(1'-(Z)-hexadecenyl)-2-(2-trimethylsilanylethoxymethyl)glycerol 

Relevant academic research and scientific papers

Regioselective phosphorylation of: Myo -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

A regioselective phosphorylation method for myo-inositol was developed by utilizing readily preparable BINOL-derived phosphoramidites. The method also facilitated the complete separation of the diastereomeric products by simple chromatography. Based on this phosphorylation and Ni-catalyzed alkyl-alkyl cross-coupling reaction for long fatty acids, we achieved the first synthesis of a lysophosphatidylinositol, EhPIa having long fatty acid C30:1, as a partial structure of glycosylphosphatidylinositol (GPI) anchor from the cell membrane of a protozoa, Entamoeba histolytica.

Direct synthesis of plasmenylcholine from allyl-substituted glycerols

We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1′-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxy-protected 1-allylglycerol precursors with s-BuLi at -65 to -80°C. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of γ-coupled, Z-vinyl ethers as the major product and α-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.