595605-41-7Relevant academic research and scientific papers
Direct synthesis of plasmenylcholine from allyl-substituted glycerols
Shin, Junhwa,Thompson, David H.
, p. 6760 - 6766 (2003)
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.
Monoallylation of 1,2-diols by Pd/Sn bimetallic catalysis
Kuriyama, Masami,Takeichi, Tsubasa,Ito, Masaaki,Yamasaki, Noritsugu,Yamamura, Ryota,Demizu, Yosuke,Onomura, Osamu
supporting information; experimental part, p. 2477 - 2480 (2012/04/04)
Efficient and mild: The selective monoallylation of 1,2-diols was successfully developed with Pd/Sn bimetallic catalysis in good to excellent yields. This process was carried out with high substrate tolerance under mild conditions (see scheme). The catalyst system achieved the quite high chemoselectivity even in the presence of a 1:1 mixture of the 1,2-diol and mono-ol. Copyright
