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Updated: Mar 18, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Investigation of α-Thioglycoside Donors: Reactivity Studies toward Configuration-Controlled Orthogonal Activation in
Raymond Smith1, Helge Müller-Bunz1, Xiangming Zhu1
1Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin , Belfield, Dublin 4, Ireland.
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.
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