Abstract
The synthesis of a mannose-capped disaccharide containing a thiol-terminated aglycon was carried out to provide a tethered sugar suitable for attaching to gold nanoparticles to mimic carbohydrate-involved cell-surface interactions. The molecule was constructed via Schmidt glycosylation of an appropriately protected glycosyl donor and an acceptor, followed by radical addition to introduce a thiol-terminated aglycon. Subsequent removal of the N-phthaloyl protective group followed by N-acetylation afforded the corresponding disaccharide 10. Removal of the O-acetyl groups and purification gave the desired target disaccharide 11 in an excellent yield, thus furnishing a sample needed for gold nanoparticle development.
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