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Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility

Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility,10.1016/j.carres.2011.04.018,Carbohydrate Resea

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Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility   (Citations: 1)
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Propargyl glyco 1,2-orthoesters were exploited for the efficient synthesis of interesting glycomonomers such as glyco-acrylates and acrylamides using gold catalysts. It was observed that propargyl glyco 1,2-orthoesters with hydroxyethyl acrylates gives very good yield of the corresponding glyco-acrylates in a single step in the presence of catalytic amount of gold(III) catalyst; whereas, gold catalyzed glycosidation reaction on hydroxyethyl acrylamides was found to yield the corresponding acrylamidoyl 1,2-orthoester which was then converted to the corresponding glycol-acrylamide in the presence of catalytic amount of TMSOTf. Synthesized glyco-acrylate/acrylamide monomers are shown to undergo thiolate addition as well as free radical polymerization.
Journal: Carbohydrate Research - CARBOHYD RES , vol. 346, no. 12, pp. 1511-1518, 2011
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