Synthesis of sugar–organometallic conjugates: ferrocenyl derivatives

Abstract

Ferrocenylcarbonyl chloride (1) reacts with 2,3,4,6-tetra-O-acetyl-l-thio-β-D-glucopyranose (2) to form the thio ester (3), and the reaction of NN-dimethylaminomethylferrocene methiodide (4) with 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose (5) yields the NN-bis-complex (6); the reaction of (2) with the ferrocenyl reagent (7) yields the sugar-ferrocenyl conjugate (8)via the versatile coupling reagent cyanuric chloride.