Brønsted acid-promoted glycosylations of disaccharide glycal substructures of the saccharomicins.
An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Bradley R
BR
Balthaser
Frank E
FE
McDonald
D039903:Actinobacteria / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004187:Disaccharides / Q000737:chemistry; D005643:Fucose / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D004187:Disaccharides; D009844:Oligosaccharides; C545617:saccharomicin A; D005643:Fucose