Borylated Monosaccharide 3-Boronic-3-deoxy-d-galactose: Detailed NMR Spectroscopic Characterisation, and Method for...

Drug leads with a high Fsp³ index are more likely to possess desirable properties for progression in the drug development pipeline. This paper describes the first detailed NMR analysis of the borylated intermediate 3-deoxy-3-boronodiethanolamine-1,2:5,6-di-O-isopropylidene-α-d-galactofuranose and of the corresponding free monosaccharide analogue 3-boronic-3-deoxy-d-galactose in the early stage of the concurrent equilibrium processes of mutarotation and borarotation. A discussion of all potential equilibria is also presented alongside a comparison with relevant ¹¹B-NMR data available from the scientific literature and our own library.