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2 protocols using chloromethyl chlorosulfate

1

Synthesis and Characterization of Squalene Derivatives

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All the chemicals used were of analytical grade. Squalene (SQ), diglycolic anhydride, ethyl chloroformate, chloromethyl chlorosulfate, ammonium acetate, n-Bu4NHSO4, TES, and triethylamine (TEA) were purchased from Sigma-Aldrich (France). Pd-C was obtained from Alfa Aesar (France). DiD and DiR were purchased, respectively, from PromoKine (Germany) and Interchim (France). Roti-Histofix 4% (formaldehyde) was provided by Roth (Germany).
All the drugs used were of analytical grade. Morphine sulfate salt pentahydrate, λ-carrageenan, naloxone hydrochloride (Nal, μ, δ, and κ opioid receptors antagonist), and naloxone methiodide (Nal-M, a nonspecific opioid receptor antagonist that does not cross the BBB) were purchased from Sigma-Aldrich (Saint-Quentin-Fallavier, France). Ketamine and xylazine were purchased from Centravet (Maisons-Alfort, France). LENK and Alloc-LENK were purchased from Ontores Biotechnologies (Zhejiang, China).
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2

Synthesis of Novel Functionalized Compounds

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Acetic acid, β-alanine, 1-aminopropan-2-ol, 3-azidopropanol, 2,2′-azobis(2-methylpropionitrile), 6-(Boc-amino)hexanoic acid, chloromethyl chlorosulfate, chloromethyl pivalate, dibenzocyclooctyne-amine, dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine, ethyl chloroformate, ethyldiisopropylamine, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, methacryloyl chloride, mebendazole, 4-nitrobenzyl chloroformate, phosgene solution, silica gel, sodium hydride, tetrabutylammonium hydrogen sulfate, tetramethylurea, thiazolidine-2-thione, and trifluoroAcetic acid were purchased from Sigma-Aldrich (Prague, Czech Republic). Acetonitrile, methanol and other common solvents and chemicals were purchased from Merck (Prague, Czech Republic). All chemicals and solvents were of analytical grade.
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