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Trichloroisocyanuric acid (TCCA) – TMSOTf: An efficient activator system

Detailed experimental content as following: After 40 mins the mixture was cooled to -5oC and Trichloroisocyanuric acid(TCCA) (35 mg, 0.15 mmol) was added to it. Then TMSOTf (8.2 μL, 0.05 mmol) was added via a micro-syringe. After the acceptor was consumed completely (checked by TLC) the reaction was quenched by triethylamine (80 μL). Molecular sieves were filtered off through celite bed. The filtrate was diluted with CH2Cl2 and washed subsequently with saturated NaHCO3 solution and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the glycosylated product. The crude mass was purified by silica gel column chromatography (60-120 mesh) (PE/EtOAc 5:1) to get pure product (3, 137.6 mg) in 95% yield. 

The scale-up experiment was done following the above reaction procedure using 1 (1.38 g, 2.37 mmol), 2 (1 g, 1.98 mmol), 4? molecular sieves, Trichloroisocyanuric acid(TCCA) (460.1 mg, 1.98 mmol) and TMSOTf (107.5 μL, 0.59 mmol) in dry CH2Cl2 (30 ml). After completion the reaction was quenched by triethylamine (1.08 mL). Pure chromatographed product (3, 1.79 g) was obtained as before in 94% yield. It was crystallized from PE/EtOAc; mp 232-234 oC. A mixture of 4 (201.0 mg, 0.286 mmol), 5 (50.0 mg, 0.238 mmol) and flame activated 4? molecular sieves in dry CH2Cl2 (4 mL) were stirred at room temperature under argon atmosphere. After 40 min the mixture was cooled to -5oC and Trichloroisocyanuric acid(TCCA) (55.3 mg, 0.238 mmol) followed by TMSOTf (12.9 μL, 0.071 mmol) were added to it. 

Trichloroisocyanuric acid(TCCA), is an efficient, broad-spectrum, safer disinfection against bacteria, viruses, fungi, spores and others have killing effect on coccidia oocysts also have some role in the killing. TCCA  biocidal effect of hypochlorite and chlorine, just as an oxidizing biocides, and the storage stability, ease of use, good solubility, good compatibility compatibility. Trichloroisocyanuric sodium cyanuric acid is a strong oxidant and chlorinating agent, is an efficient, broad-spectrum, safer disinfection against bacteria, viruses, fungi, spores and others have killing effect on coccidia oocysts there is a certain role in the killing. TCCA  with Gaisu pail lined with plastic film, net weight 50kg.