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2,4,6-Triisopropylbenzenesulfonyl chloride is used for the synthesis of glycerophospholipids as a condensing agent and in the analysis of phosphonolipids in egg yolk by HPLC/MS technique. It acts as a coupling reagent for the synthesis of oligonucleotides and as sulfonates of pyrimidine nucleosides. It also serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters.
Hindered sulfonyl chlorides have found use as condensing agents for the formation of the phosphate link of oligonucleotides. For reviews, see: Angew. Chem. Int. Ed., 11, 451 (1972); Synthesis, 222 (1975); Chem. Rev., 77, 183 (1977). For reviews of oligonucleotide synthesis by the phosphotriester method, see: Heterocycles, 7, 1197 (1977); Tetrahedron, 34, 3143 (1978). For use as a condensing agent in the synthesis of H-phosphonate diesters, see: Nucleosides Nucleotides, 7, 23 (1988). More hindered in comparison with, e.g. Mesitylene-2-sulfonyl chloride, A11775, and so has less tendency to react with the free 5'-hydroxyl group of sugars: J. Am. Chem. Soc., 88, 829 (1966).
For examples of the utility of the triisopropylbenzenesulfonyl group in the protection of OH groups, see: J. Am. Chem. Soc., 117, 5693, 5776 (1995): (first synthesis of a digitalis saponin and asymmetric synthesis of (-) and (+)-strychnine, respectively)./n
Cai, H.; Liu, Q.; Gao, D.; Wang, T.; Chen, T.; Yan, G.; Chen, K.; Xu, Y.; Wang, H.; Li, Y.; Zhu, W. Novel fatty acid binding protein 4 (FABP4) inhibitors: Virtual screening, synthesis and crystal structure determination. Eur. J. Med. Chem. 2015, 90, 241-250.
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