The Ramberg-Bäcklund reaction for the synthesis of C-glycosides, C-linked-disaccharides and related compounds.
The discovery of the Ramberg-Bäcklund 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 beta-glycosidase inhibitors, spirocyclic glucose derivatives, beta-C-glycosides, C-glycosyl porphyrin glycoconjugates and C-glycosyl amino acids, are also discussed. Finally, applications of the Ramberg-Bäcklund process for the synthesis of known and novel C-glycosides, and in natural product synthesis, are reviewed.
Taylor
Richard J K
RJ
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. rjkt1@york.ac.uk
McAllister
Graeme D
GD
Franck
Richard W
RW
D000475:Alkenes / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis; D004187:Disaccharides / Q000138:chemical synthesis*; D005989:Glycerides / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry
D000475:Alkenes; D000596:Amino Acids; D004187:Disaccharides; D005989:Glycerides; D006027:Glycosides; D013450:Sulfones