title: Comparing the use of 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl and 2,4,6-trimethoxybenzyl as N-H protecting groups for p-tolyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucosides.
abstract: A hurdle in glycosylation reactions of 2-acetamido glycosyl donors is the formation of a stable and unreactive oxazoline that decreases the yield of these reactions significantly. As an effort to prevent oxazoline formation during glycosylation reactions, we protected the N-H of the acetamido group within a 2-acetamido-2-deoxy-1-thio-β-D-glucoside with one of four different protecting groups. These groups were either 2-methylenenapthyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl or 2,4,6-trimethoxybenzyl. The resulting N-alkylacetamides were then used in glycosylation reactions with ethanol as a model acceptor. We observed that the ethyl glycosides obtained in each case were obtained with exclusive β-selectivity without the formation of oxazoline sideproducts. The resulting products were then used to screen conditions for protecting group removal.
authors.affiliation: Department of Chemistry, The University of Toledo, OH 43606, USA.
authors.forename: Sourav
authors.initials: S
authors.lastname: Sarkar
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Sucheck
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013863:Thioglucosides / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D009281:Naphthalenes; D009844:Oligosaccharides; D013863:Thioglucosides