title: Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker.
abstract: A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone.
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre Edmonton, AB T6G 2G2 (Canada) E-mail: tlowary@ualberta.ca.
authors.forename: Junfeng
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre Edmonton, AB T6G 2G2 (Canada) E-mail: tlowary@ualberta.ca.
authors.forename: Lu
authors.initials: L
authors.lastname: Zou
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre Edmonton, AB T6G 2G2 (Canada) E-mail: tlowary@ualberta.ca.
authors.forename: Todd L
authors.initials: TL
authors.lastname: Lowary
keywords: activated esters; immunomodulatory glycans; lacto-N-fucopentaose III (LNFPIII); oligosaccharides; regioselective glycosylation