Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility
Title | Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility |
Publication Type | Journal Article |
Year of Publication | 2011 |
Authors | Thadke, SA, Kar, M, Gupta, SSen, Hotha, S |
Journal | Carbohydrate Research |
Volume | 346 |
Issue | 12 |
Pagination | 1511-1518 |
Date Published | SEP |
ISSN | 0008-6215 |
Keywords | carbohydrates, Glycoacrylamides, Glycoacrylates, Glycopolymers, glycosylation, Gold |
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 (C) 2011 Elsevier Ltd. All rights reserved. |
DOI | 10.1016/j.carres.2011.04.018 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 2.70 |