Preparation of iminosugars from aminopolyols via selective oxidation using galactose oxidase

Abstract

Minimally protected aminopolyols are novel substrates for the galactose oxidase variant F₂. Site-selective oxidation proceeds at the terminal primary alcohol, followed by spontaneous cyclisation to afford stable hemiaminal/hemiacetal anomers of the piperidine and azepane scaffolds, with isolated yields of up to 94%. Simultaneous deprotection and reduction occured readily to afford valuable and biologically relevant iminosugars.