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

TitleGold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility
Publication TypeJournal Article
Year of Publication2011
AuthorsThadke, SA, Kar, M, Gupta, SSen, Hotha, S
JournalCarbohydrate Research
Volume346
Issue12
Pagination1511-1518
Date PublishedSEP
ISSN0008-6215
Keywordscarbohydrates, 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.

DOI10.1016/j.carres.2011.04.018
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.70
Divison category: 
Chemical Engineering & Process Development
Organic Chemistry