Soluble imidazolium cations (ImC) have shown potential as supports for catalyst or reagent immobilization and their utility in solution phase synthesis. The solubility of ImC 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, ImC tagged carbohydrate species containing non-coordinating anion such as PF6- or BF4- 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 ImC tagged glycosides by NMR and ESIMS spectroscopic techniques. Herein, we report a convergent orthogonal approach to the assembly of the target nonasaccharide from Corynebacterium glutamicum using the ImC supported acceptor mannose. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/4402_figure_1.jpg' alt='' />

Imidazolium cation tagged solution-phase assembly of oligosaccharide from Corynebacterium glutamicum

241st National Meeting (2011)

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