Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility |
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Authors: | Thadke Shivaji A Kar Mritunjoy Gupta Sayam Sen Hotha Srinivas |
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Institution: | aDivision of Organic Chemistry, Combi Chem-Bio Resource Center, National Chemical Laboratory, Pune 411 008, India;bDivision of Chemical Engineering & Process Development, National Chemical Laboratory, Pune 411 008, India;cDepartment of Chemistry, Indian Institute of Science Education & Research, Pune 411 021, India |
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Abstract: | 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. |
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Keywords: | Glycopolymers Carbohydrates Glycosylation Glycoacrylates Glycoacrylamides Gold |
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