Polymer-supported tin carbohydrate chemistry |
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Authors: | D.M. Whitfield T. Ogawa |
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Affiliation: | (1) National Research Council, Ottawa Ontario, Canada, K1A 0R6;(2) The Institute of Physical and Chemical Research (RIKEN), Wako-shi Saitama, 351, Japan |
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Abstract: | It was anticipated that stannylation of carbohydrates could be achieved using tin on a polymer-support. Such immobilization simplifies the purification of the carbohydrate because the toxic tin reagent can be removed by filtration. In this case an alkene linker (3-buten-1-ol) was added to chloromethylated 2% cross-linked polystyrene by etherification. Photochemical hydrostannylation with dibutyltinchlorohydride gave a polymer bound trialkyl tin chloride. The Sn-Cl could be hydrolysed with NaOH to yield a resin with terminal Sn-O bonds. Highly regioselective acylation of methyl -D-mannopyranoside (MeMan) to its 3-O-benzoyl derivative was achieved. Traces of the mono 6-O-benzoate and the 3,6-di-O-benzoate were also obtained. Methyl -D-glucopyranoside was also selectively acylated to its 2-O-benzoate but this reaction gave a more complex mixture. The isolated yields (10–30% based on sugar) were disappointingly low. The yields were improved to about 60% with 5% cross-linked resin. |
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Keywords: | polymer-support tin stannylation |
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