Zinc triflate-promoted glycosidation: synthesis of lipid A disaccharide intermediates.
Zinc triflate was found to be superior to the heavy metal salts as a promoter in the Koenigs-Knorr type glycosidation reaction in the synthesis of lipid A disaccharide intermediates. It readily promoted the reaction of a complex glycosyl bromide with a reducing sugar moiety and gave the disaccharide with beta-selectivity in good yield. This method would be suitable for the bulk preparation of lipid A disaccharide intermediates.
Nakayama
K
K
Exploratory Research Laboratories I, Daiichi Pharmaceutical Co. Ltd., Tokyo, Japan.
Higashi
K
K
Soga
T
T
Uoto
K
K
Kusama
T
T
D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000138:chemical synthesis*; D006031:Glycosylation; D008050:Lipid A / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008698:Mesylates / Q000737:chemistry*; D008969:Molecular Sequence Data; D013055:Spectrophotometry, Infrared; D015032:Zinc / Q000737:chemistry*
D004187:Disaccharides; D008050:Lipid A; D008698:Mesylates; D015032:Zinc; C012077:trifluoromethanesulfonic acid