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N-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation
Authors:Barrie Kellam  Paul A Ward  Aisyah S Abdul Rahim  Siri Ram Chhabra
Institution:School of Pharmacy, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK
Abstract:Nα-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, l-threonine and l-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient α-O-glycosylation with an l-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis.
Keywords:Protecting groups  Glycosylation  Amino acids and derivatives
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