Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 10, Pages 1235-1252Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.04.008
Keywords
aluminum aldolate; carbonylative stille coupling; combinatorial synthesis; core-B structure; fluoro-C-linked disaccharides; C-glycosyl donor; Lemieux azidation; Takai-Hiyama-Nozaki-Kishi coupling; Thomsen-Friedenreich epitope; Oshima-Nozaki three-component condensation
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Because of their functionalities (enone, ketone, and acetal) and their bicyclic structure (steric factors), levoglucosenone (1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyran-2-ulose) and isolevoglucosenone (1,6-anhydro-2,3-dideoxy-beta-D-glycero-hex-3-enopyran-4-ulose) are useful templates for the convergent and combinatorial synthesis of (1 -> 2), (1 -> 3), and (1 -> 4)-linked C-disaccharides in reactions combining them with sugar-derived carbaldehydes. Synthetic methods relying on conjugate nucleophilic additions of these enones, their combination with aluminum reagents and aldehydes (Baylis-Hillman reaction) and modified Takai-Hiyama-Nozaki-Kishi couplings of enol triflates derived from them with sugar-derived aldehydes are reviewed. Highly stereoselective methods have thus been developed. These allow the generation of disaccharide mimetics with a high molecular diversity. (c) 2006 Elsevier Ltd. All rights reserved.
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