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Synthesis of sugar-organometallic conjugates: ferrocenyl monosaccharide derivatives.
Suitably blocked carbohydrates containing free thio 4, amino 5, and hydroxyl 10,19 nucleophilic functionalities have been treated with (a) ferrocenecarbonyl chlorides 2 and 3. (b) N,N-dimethylaminomethylferrocene methiodide 12, and (c) ferrocenyl tosylate 16 to form the ferrocenyl sugar derivatives 6,7,8,9,11,13,14,15 and 20.Direct conjugation of a free, water-soluble sugar to ferrocene was achieved by the formation of a Schiff’s base between glucosamine hydrochloride 25 and ferrocene carboxaldehyde 24.The synthesis of ferrocenyl sugars using bridging group technology is exemplified by the conjugation of the thio sugar 4 to ferrocene via the versatile coupling reagent cyanuric chloride 21 to form the s-triazine compound 23.These products have been studied by 1H nmr spectroscopy: chemical shifts, coupling constants, and proton spin-lattice relaxation measurements.
Synthesis of sugar-organometallic conjugates: ferrocenyl monosaccharide derivatives.
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Reference£º
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion