1997 年 55 巻 8 号 p. 705-713
Recently, inositol phospholipids in the plasma membrane have received much attention due to their biological interests in signal transduction systems. In order to accomplish efficient syntheses of the target lipids, a selective phosphorylation methodology via phosphonium salt and glycosylation method using glycosyl phosphite as a glycosyl donor were developed based on the phosphite chemistry. New benzoyl derivatives bearing oxyethyl substituents at the ortho position, so called PAC were devised for protecting hydroxyl groups. They can be removed chemoselectively by an intramolecular cyclization mode even in the presence of an acyl group and also function as an auxiliary in the diastereoselective acylation using a monomethyl tartrate derivative. Employing these synthetic strategies, synthesis of phosphatidylinositol 3, 4, 5-trisphosphate, 4, 5-bisphosphate, and 2, 6-dimannopyranosylphosphatidylinositol were achieved in an efficient and concise manner.