The synthesis of neoglycophospholipid conjugates via reductive amination of ω-oxoalkylglycosides and phosphatidylethanolamines

Phospholipid conjugates of mono- and disaccharides tethered with an n-decanyl spacer were efficiently synthesized via an improved reductive amination of deprotected ω-oxodecanyl β-glycosides and phosphatidylethanolamines with or without alkenyl groups. The ω-oxodecanyl β-glycosides were prepared by stereoselective glycosidation of glycosyl halides with 1,10-decanediol followed by pyridinium dichromate oxidation. The acetyl groups of the ω-oxodecanyl β-glycosides were removed with sodium methoxide prior to their conjugation with phosphatidylethanolamines.