Preparation and proton magnetic resonance spectra of the methyl ethers of 1,6-anhydro-β-D-glucopyranose

Abstract

The seven methyl ethers of 1,6-anhydro-β-D-glucopyranose have been prepared and their proton magnetic resonance spectra examined. Additive rules have been derived and used successfully to predict the chemical shifts of the ring protons. I.r. hydroxy-stretching frequencies of the monomethyl and dimethyl ethers have been measured. Intramolecular hydrogen bonding can be invoked to explain the selective esterification of 1,6-anhydro-β-D-glucopyranose with acid chlorides in pyridine.