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2,4,6-Trichlorobenzoyl chloride is used in the preparation of γ-lactone and δ-lactone, aliphatic aromatic anhydrides, required for the synthesis of amphiphilic hyaluronan, mixed anhydride, required for the synthesis of angelate esters, synthesis of both spongistatin 1 and spongistatin 2 and large-ring lactones in high yields.
Gloria Huerta-Angeles.; Martin Bobek.; Eva P?íkopová.; Daniela Šmejkalová.; Vladimír Velebný. Novel synthetic method for the preparation of amphiphilic hyaluronan by means of aliphatic aromatic anhydrides. .Carbohydrate Polymers 2014, 111 883-891.
Machiko Ono.; Keisuke Kato.; Hiroyuki Akita. Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy. Chemical & Pharmaceutical Bulletin. 2013, 61 (4), 464-470.
Reagent, introduced by Yamaguchi, which forms mixed anhydrides with acids, useful in the synthesis of esters: Bull. Chem. Soc. Jpn., 52, 1989 (1979), or lactones including macrolides: Chem. Lett., 1021 (1979). Superior to mesitylenesulfonyl chloride for macrolactonization, which has been achieved in the presence of DMAP without the need for high dilution: J. Org. Chem., 55, 7 (1990); Tetrahedron Lett., 31, 6367 (1990).
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant