Journal
CARBOHYDRATE RESEARCH
Volume 341, Issue 10, Pages 1298-1311Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.03.013
Keywords
exo-glycals; synthesis; glycosides; disaccharides; glycosyl amino acids; one-pot processes
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The discovery of the Ramberg-Backlund procedure for preparing exo-glycals from S-glycoside dioxides, developed independently in (Old) York and New York, is reviewed. The methodology is successful with glucose, galactose, mannose, xylose, fucose, ribose, altrose, 2-deoxy-arabino-hexose (2-deoxy-glucose) and daunosamine derivatives, and has been used to prepare di-, tri- and tetra-substituted exo-glycals. More recent developments, such as one-pot variants, and protecting group-free procedures, are also covered. Synthetic applications of the exo-glycals, for example, to prepare P-glycosidase inhibitors, spirocyclic glucose derivatives, P-C-glycosides, C-glycosyl porphyrin glycoconjugates and C-glycosyl amino acids, are also discussed. Finally, applications of the Ramberg-Backlund process for the synthesis of known and novel C-glycosides, and in natural product synthesis, are reviewed. (c) 2006 Elsevier Ltd. All rights reserved.
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