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Mesitylene-2-sulfonyl chloride is used as reagent for intramolecular lactamizations and lactonization. It also acts as a reagent for protecting guanidino groups and tryptophan. It is used as coupling reagent in polynucleotide synthesis
Chi-Hua Wang; Saul G. Cohen. Mercaptan Catalysis in Thermoneutral Free Radical Exchange.J. Am. Chem. Soc. 1957, 79 (8),1924-1929.
Adeleh Kiania; Batool Akhlaghiniaa; Hamed Rouhi-Saadabada & Mehdi Bakavolia.Journal of Sulfur Chemistry. 2014, 35 119-127.
Selective reagent for sulfonylation of carbohydrates: J. Chem. Soc., Perkin 1, 1373 (1974).
For reviews of the use of hindered sulfonyl chlorides as condensing agents for the formation of the phosphate link of oligonucleotides, 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). Compare 2,4,6-Triisopropylbenzenesulfonyl chloride, A11458.
Reagent for protection of the guanidino function of arginine residues as mesitylenesulfonyl (Mts) derivatives in peptide synthesis: J. Chem. Soc., Chem. Commun., 482 (1978); Chem. Pharm. Bull., 26, 3752 (1978); Int. J. Pept. Prot. Res., 14, 169 (1979). Deprotection can be effected with triflic acid in TFA in the presence of thioanisole as a cation scavenger: J. Chem. Soc., Chem. Commun., 1063 (1980).
The indole nitrogen, e.g. in tryptophan residues, may also be protected as the Mts amide, stable to dilute alkali, hydrazine hydrate, TFA, 4N HCl in dioxane, or HBr in AcOH, but cleaved by MsOH, or TfOH in TFA: Chem. Pharm. Bull., 32, 2660 (1984). See Appendix 6.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.