Imidazolium cations (IC) have shown potential as supports for catalyst or reagent immobilization and their utility in solution phase 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 PF6- can be purified from the reaction mixture by simple washing after concentration with solvents such as diethylether and water. 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 NMR and ESIMS spectroscopic techniques. Herein, we report a convergent orthogonal approach to the assembly of the branched nonasaccharide from Corynebacterium glutamicumusing the IC supported acceptor mannose 

Imidazolium cation tagged solution-phase assembly of branched nonasaccharide from Corynebacterium glutamicum

246th National Meeting (2013)

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