Organic Letters 2010-11-19

Adaptable synthesis of C-glycosidic multivalent carbohydrates and succinamide-linked derivatization.

Gavin J Miller, John M Gardiner

Index: Org. Lett. 12(22) , 5262-5, (2010)

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Abstract

A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].