Soluble imidazolium cations (IC) have shown potential as supports for catalyst or reagent immobilization and their utility in solution phase oligosaccharide synthesis. The solubility of IC tagged organic species can be turned on and off by variation of anions to make them phase separate from less polar organic solvents such as chloroform/dichloromethane and aqueous media. Thus, IC tagged carbohydrate species containing non-coordinating anion such as hexafluorophosphate can be purified from the reaction mixture after conventional workup and concentration by simple washing with solvents such as diethylether. This methodology provides; a) homogeneous reaction conditions, b) eliminates the excessive use of column chromatography for the purification of products after each glycosylation step, and c) convenient characterization of IC tagged glycosides by conventional spectroscopic techniques. Herein, we report a convenient IC-tagged assembly of the target branched nonasaccharide from Corynebacterium glutamicum using an efficient catch and release purification on Silica gel.

Efficient imidazolium cation tagged solution-phase assembly of a nonasaccharide

243rd National Meeting (2012)

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