A general method for determining the anomeric configuration of C-furanoside derivatives: a 1H nuclear magnetic resonance nuclear Overhauser effect study

Abstract

The nuclear Overhauser effect ¹H n.m.r. experiment was found to be an excellent method for a priori determination of the stereochemical configuration of a variety of C-furanoside derivatives. If the stereochemistry at one ring carbon atom is known, the methine proton at this centre may be used to determine the proton stereochemistry at neighbouring carbon centres and this can be repeated until the anomeric proton configuration is determined. Certain protecting groups themselves may be used to report on the C-furanoside anomeric configuration, and this was demonstrated with methoxymethyl and O-isopropylidene derivatives.