title: Investigation of α-Thioglycoside Donors: Reactivity Studies toward Configuration-Controlled Orthogonal Activation in One-Pot Systems.
abstract: The influence of anomeric configuration upon thioglycoside donors remains relatively unexplored. Utilizing methodology developed for the stereoselective and high-yielding synthesis of α-glycosyl thiols, a series of α-thioglycosides were synthesized, and their reactivity was compared to that of their β-counterparts. The highly selective activation observed for anomeric pairs containing a 2-O-acyl moiety and additional findings are reported. Application of a pair of "superarmed" thioglycosides to a one-pot oligosaccharide system is also described, in which selectivity is a result of configuration-based orthogonal activation.
authors.affiliation: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors.forename: Raymond
authors.initials: R
authors.lastname: Smith
authors.affiliation: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors.forename: Helge
authors.initials: H
authors.lastname: Müller-Bunz
authors.affiliation: Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
authors.forename: Xiangming
authors.initials: X
authors.lastname: Zhu