Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation.
[formula: see text] The synthesis of an all-alpha L-oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.
McDonald
Frank E
FE
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA. fmcdona@emory.edu
Wu
Minglang
M
D000143:Acids; D003500:Cyclization; D004074:Digitoxin / Q000737:chemistry; D005643:Fucose / Q000737:chemistry; D006031:Glycosylation; D013237:Stereoisomerism; D014312:Trisaccharides / Q000138:chemical synthesis*
D000143:Acids; D014312:Trisaccharides; C478028:galactopyranosyl-1-3-glucopyranosyl-1-2-fructofuranose; D005643:Fucose; D004074:Digitoxin