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Preparation of iminosugars from aminopolyols via selective oxidation using galactose oxidase

2022-11-07, Yeow, Kathryn, Haarr, Marianne B., Muldoon, Jimmy, O'Reilly, Elaine

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.