Synthesis of double-tailed (perfluoroalkyl)alkyl phosphosugars: new components for drug-carrying and -targeting systems

Synthesis of phospholipids containing perfluorooctyl group and their interfacial properties

“…2-Bromoethylphosphorodichloridate was prepared by the method of Baumann and co-workers [10]. (E)-and (Z)- 11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-heptadecafluoro-9-octadecen-1-ol (E-6 and Z-6), 11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-heptadecafluoro-9-octadecyn-1-ol (7), 11,11,12,12,13,13,14,14,15,15,16,16,17,17,18, 18,18-heptadecafluoro-9-iodooctadecan-1-ol (8), and 11,11, 12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-heptadecafluorooctadecan-1-ol (9) were synthesized according to our previous report [5], and were assigned by 1 H and 19 F NMR. The precursor of 15, 9-octadecyn-1-ol, was synthesized from octyl bromide and lithium acetylide of 9-decyn-1-ol [20].…”

“…2) since phospholipids are expected to be more biocompatible than fatty acids. Although the synthesis of several phosphorylated perfluoroalkyl amphiphiles has been reported [1,[6][7][8][9], phosphorylated amphiphiles containing highly fluorinated C 18 alkyl chains, of which the chain length is considered to be compatible with biomembrane components, have not been synthesized or reported so far.…”

Small-Angle Scattering and Electron Microscopy Investigation of Nanotubules Made from a Perfluoroalkylated Glucophospholipid

“…F-Glu was a gift from Prof. J. G. Riess (UCSD, San Diego, CA). Its synthesis was reported in Ref (30). Water was deionized with an Elgastat purification system.…”

Synthesis, emulsification and self-assembly properties of sugar-containing semifluorinated amphiphiles

“…12-16 Our goal was two-fold – first, it was to investigate the use of saccharide-perfluoroalkyl amphiphiles with respect to the sevoflurane-perfluorooctyl bromide system, and second, it was to explore convenient methods of introducing a perfluoroalkyl chain into a saccharide-based hydrophilic head. Perfluoroalkyl chains have been installed into saccharides by a number of different chemistries: glycosylation, 17-22 formal glycosylation, 23-24 ether formation, 13,14,25 ether formation by way of radical addition, 14,26 acetal formation, 27 carbon-carbon bond formation, 28 urea, 29,30 thiourea 29,31 and carbamate 32 formation, phosphoester formation, 33-35 ester 15,26,36 and amide 23,37-39 formation, as well as thiol-initiated Michael 40 and free radical 41 addition. In this study we report the synthesis of novel fluoroalkyl sugars surfactants by using Cu-catalyzed azide-alkyne cycloaddition.…”