title: Achiral 2-Hydroxy Protecting Group for the Stereocontrolled Synthesis of 1,2-cis-α-Glycosides by Six-Ring Neighboring Group Participation.
abstract: Glycosylation of a fully armed donor bearing a 2-O-(trimethoxybenzenethiol) ethyl ether protecting group is completely α-selective with a range of carbohydrate alcohol acceptors. Low-temperature NMR studies confirm the intermediacy of cyclic sulfonium ion intermediates arising from six-membered β-sulfonium ring neighboring group participation. Selective protecting group removal is achieved in high yield in a single operation by S-methylation and base-induced β-elimination.
authors: Department of Chemistry and ‡Biomolecular Interaction Centre, University of Canterbury , Private Bag 4800, Christchurch 8140, New Zealand.
authors: Govind P
authors: GP
authors: Singh
authors: Department of Chemistry and ‡Biomolecular Interaction Centre, University of Canterbury , Private Bag 4800, Christchurch 8140, New Zealand.
authors: Andrew J A
authors: AJ
authors: Watson
authors: Department of Chemistry and ‡Biomolecular Interaction Centre, University of Canterbury , Private Bag 4800, Christchurch 8140, New Zealand.
authors: Antony J
authors: AJ
authors: Fairbanks
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D006027:Glycosides