Toluenesulfonyl Chloride and Related Reagents, Polymer-supported

John E. Toth Elizabeth A. Collins Eli Lilly and Company, Indianapolis, IN, USA 

Alternate Name polymer-supported tosyl chloride, PS-TsCl, PS-SO2CI. 

Solubility compatible with CH2CI2, THE, DMF, and other swelling solvents. 

Preparative Methods commercially available prepared from sul-fonated ion exchange resins (e.g., Dowex) via chlorination  

Solid-phase Oligosaccharide Synthesis. Methanesulfonyl chloride resin 1 was used as an activating linker in the synthesis of various polymer-bound di and trisaccharides 2 (eq 1). The sulfonate linker proved stable to glycosidation and alcohol deprotection conditions, and nucleophilic displacement of 2 by Nal provided 6-iodosaccharides (eq 1). NaOAc and NaNs were also suitable nucleophiles for cleavage of the sulfonate linker.  

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