Synthesis of Functionalized Lipids,and Their Use for a Tunable Hydrophobization of Nucleosides and Nucleic Acids

Two series of functionalized single and double side‐chained lipid molecules (Schemes 1 and 2) were prepared. The compounds carry either terminal COOH, OH, or halogen substituents. Moreover, the double side‐chained lipid 18 carries an internal alkyne functionality. The latter compound was used to hydrophobize thymidine at N(3) by base‐catalyzed alkylation. Additionally, fully protected thymidine, 32 , was N(3)‐alkylated with the double side‐chained alcohol 9 applying Mitsunobu reaction conditions.