A new route to aminosugars from sugar nitrones: synthesis of 6-deoxynojirimycin

Abstract

The 1,3-addition of methylmagnesium chloride to dialdose derived nitrones 3 and 7 afforded N-benzylhydroxylamines 4/5 and 8/9, respectively, in high yields. The stereoselectivity of the addition reaction was improved by the use of trimethylsilyl triflate. The N---O bond reductive cleavages of N-benzylhydroxylamines took place in good yields and offered an easy access to N-benzylaminosugars. The potential of these aminosugars is demonstrated by the synthesis of glycosidase inhibitor 6-deoxynojirimycin 1a.