595605-52-0Relevant academic research and scientific papers
Direct synthesis of plasmenylcholine from allyl-substituted glycerols
Shin, Junhwa,Thompson, David H.
, p. 6760 - 6766 (2007/10/03)
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.
