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An efficient strategy for synthesis of spacer-armed tetrasaccharide related to galactan I of Klebsiella pneumoniae was reported employing newly developed acid-free conditions for pyranoside-into-furanoside (PIF) rearrangement of a digalactoside bearing… Click to show full abstract
An efficient strategy for synthesis of spacer-armed tetrasaccharide related to galactan I of Klebsiella pneumoniae was reported employing newly developed acid-free conditions for pyranoside-into-furanoside (PIF) rearrangement of a digalactoside bearing 4-pentenyl group at anomeric position. The 4-pentenyl aglycon was successfully used both as a leaving group in glycosylation of 3-trifluoroacetamidopropanol, and as a temporary anomeric protection, permitting its conversion into the imidate donor. Regioselective coupling of the disaccharide blocks afforded the desired tetrasaccharide sequence required for investigation of interaction of galactan I with immune system proteins.
Journal Title: European Journal of Organic Chemistry
Year Published: 2017
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