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

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
8
Issue
9
Identifiers
DOI: 10.1016/s0957-4166(97)00147-x

Abstract

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.

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