5 hexyn 1 ol

Acryloyl chloride, bis(cyclopentadienyl)titanium dichloride, 9-borabicyclo[3.3.1]nonane, 3-buten-3-ol, n-butyl acrylate, n-decan-1-ol, Dess-Martin periodinane, diethyl ether, diethylaluminium chloride, n-heptan-1-ol, 6-hepten-1-ol, 1,4-hexadiene, (E)-2-hexen-1-ol, (E)-3-hexen-1-ol, (E)-4-hexen-1-ol, 5-hexen-1-ol, 1-hexen-3-ol, 5-hexyn-1-ol, hydrogen peroxide solution, lithium diisopropylamide, magnesium sulfate, n-octan-1-ol, 1-octen-3-one, n-pentan-1-ol, 4-penten-1-ol, petroleum ether, phenoxyacetic acid, propionic acid, sodium bicarbonate, sodium thiosulfate pentahydrate, tetrahydrofuran, triethyl orthoacetate, trimethylamine, and vinylmagnesium bromide solution were purchased from Sigma-Aldrich (Steinheim, Germany). The educts 1-hepten-3-ol, 1-hexen-3-one, and 7-octen-1-ol were purchased from abcr (Karlsruhe, Germany) and chloroform, sodium hydroxide, and sulphuric acid from Carl Roth (Karlsruhe, Germany). Dichloromethane, ethyl acetate, n-hexyl acrylate, methanol, 1-nonen-3-one, n-propyl acrylate, silica gel (Normasil 60, 40–63 µm), and sodium chloride were purchased from VWR International GmbH (Darmstadt, Germany). All reactants were at least of reagent grade.

HEPES (Sigma-Aldrich, 99.5% purity, copper ≤ 5 ppm); MgCl₂.H₂O (Sigma-Aldrich, 99% purity, copper ≤ 5 ppm); LiOH·H₂O (Sigma-Aldrich, ≥ 99% purity, copper ≤ 5 ppm); sodium ascorbate (Sigma-Aldrich, 98% purity); NaCl (Sigma-Aldrich, 99% purity); KCl (ACP Chemicals, 99%); sodium acetate (Bio Basic, 99% purity); 5-hexyn-1-ol (Sigma-Aldrich, 96% purity); propargyl alcohol (Sigma-Aldrich, 99% purity); 3-azido-7-hydroxycoumarin (AK Scientific 98% purity); azide-PEG3-biotin conjugate (Sigma-Aldrich, purity not specified by the manufacturer); NaOH (Sigma-Aldrich, 99% purity); CuSO₄ (Fisher Scientific, 99% purity); Azido-PEG2-NHS ester (BroadPharm, 98% purity); Fluorescein-NHS ester (BroadPharm, 95% purity); AFDye 546 (Click Chemistry Tools, ≥95%); Lysozyme, from chicken egg white (Sigma-Aldrich, ≥ 98% purity); Nuclease P1 (NEB, 100,000 Units/mL).