Preparation of omega-functionalized eicosane-phosphate building blocks.

New 1,20-substituted eicosanes carrying phosphate headgroups and readily derivatizable thiol, maleimido, and activated carboxylic ester moieties were prepared. The C20-backbone of these molecules was assembled by a halopolycarbon homologation from 1,8-dichlorooctane and 1,6-dibromohexane. 20-Mercapto- and 20-maleimido-icosylphosphates were synthesized via omega-bromo di-t-butyl protected icosylphosphate while 20-phosphonooxy-icosanoic acid N-hydroxysuccinimidoyl ester was prepared via omega-bromo dibenzyl protected icosylphosphate in multistep syntheses. These molecules can serve as model compounds for studying binding and structural organization on different surfaces with potential applications in the fields of biosensors.