Triisopropylbenzene sulfonyl chloride

Condensation of (441) [306, 307] with 1,2-di-O-stearoyl-DL-glycerol 3-phosphate in the presence of 2,4,6-triisopropylbenzene sulfonyl chloride in pyridine gave a mixture of the required products (442) (52%) and the isomer (443) (26%) which were separated by chromatography. The anilino groups were removed from (442) by the... 

We find that j3-cyclodextrin reacts smoothly with 1-butyldimethyl-silylchloride to afford the heptasilyl derivative in which all of the primary hydroxyls are blocked. This then can be sulfonated on the secondary face for ease of separation, our preferred reagent is triisopropylbenzene sulfonyl chloride. The resulting monotrypsilated cyclodextrin is, from NMR evidence, sulfonated on hydroxyl-2. This is not easily displaced, but on treatment with base it is converted to the 2,3-epoxide, and this is relatively reactive towards nucleophiles. 

The analogue (20) has been designed as a hapten for the generation of catalytic antibodies with phosphodiesterase activity. The compound was synthesised by reaction of (21) with the phosphate diester (22) in the presence of the activating agent triisopropylbenzene sulfonyl chloride. 

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