Abstract
We present here the synthetic routes and the experimental data (NMR and MS spectra) for model reactions for copper-free Huisgen 1,4-cycloaddition, Staudinger ligation and for addition of a dithiol on a dibromomaleimide ring. Starting materials were synthesized from the commercially available 4-chlorophenethylamine, previously described 2-(cyclooct-2-yn-1-yloxy)acetic acid, 1-fluorocyclooct-2-ynecarboxylic acid, commercial 2-(diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester and dibromomaleimide. In all cases, the expected compounds were obtained with good yield (50% to quantitative). A novel synthesis of the lipid anchor DOGP3NH2 is also described. These data were used as basis for the study reported in the article “Smart Tools and Orthogonal Click-like Reactions onto Small Unilamellar Vesicles” in Chemistry and Physics of Lipids [1].
Highlights
Maria Vittoria Spanedda, Christophe Salomé, Benoît Hilbold, Etienne Berner, Béatrice Heurtault, Sylvie Fournel, Benoît Frisch, Line Bourel-Bonnet n
We present here the synthetic routes and the experimental data (NMR and MS spectra) for model reactions for copper-free Huisgen 1,4cycloaddition, Staudinger ligation and for addition of a dithiol on a dibromomaleimide ring
Analytical RP–HPLC–MS was performed using a C18 column (30 mm  1 mm; 1.9 μm) using the following parameters: (1) the eluent system A (0.05% TFA in H2O) and B (0.05% TFA in acetonitrile); (2) the linear gradient t1⁄4 0 min with 98% A, t1⁄45 min with 5% A, t1⁄4 6 min with 5% A, t1⁄47 min with 98% A, and t1⁄49 min with 98% A; (3) flow rate of 0.3 mL minÀ1; (4) column temperature 50 1C; (5) ratio of products determined by integration of spectra recorded at 210 or 254 nm; and (6) ionization mode ESI
Summary
H2O (1 mL) was added to a mixture of (Z)-1-azido-14-((Z)-octadec-9-en-1-yloxy)-3,6,9,12,16pentaoxatetratriacont-25-ene [2] (60 mg, 0.076 mmol) and triphenylphosphine polymer-supported (1.48 mmol/g, 155 mg, 0.23 mmol) in THF (5 mL). EtOH was added to the beads and the mixture was shaken (5 min). The mixture was filtered and the beads were placed again in the filtration tube. Once again CH2Cl2 was added to the beads, the mixture was shaken (5 min) and the beads were filtered. All the EtOH and CH2Cl2 layers were combined, dried and concentrated under vacuum to obtain quantitatively (Z)-14-((Z)-octadec-9-en-1-yloxy)-3,6,9,12,16-pentaoxatetratriacont-25-en-1-amine (1) as a colorless oil; 1H NMR (300 MHz, CDCl3): δ 5.35–5.30 (m, 4H), 3.64–3.40 (m, 23H), 2.05–1.90 (m, 8H), 1.60–1.52 (m, 4H), 1.40–1.19 (m, 44H), 0.86 (t, J1⁄47.1 Hz, 6H)
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
