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

Autor(en): Korneev, Sergei 
Rosemeyer, Helmut 
Stichwörter: Chemistry; Chemistry, Multidisciplinary; MITSUNOBU REACTION; PROTECTION
Erscheinungsdatum: 2013
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 96
Ausgabe: 2
Startseite: 201
Seitenende: 216
Zusammenfassung: 
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.
ISSN: 0018019X
DOI: 10.1002/hlca.201100410

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