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

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-benz...

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Published in:Tetrahedron: asymmetry 1997-05, Vol.8 (9), p.1475-1486
Main Authors: Dhavale, Dilip D, Desai, Vijaya N, Sindkhedkar, Milind D, Mali, Raghao S, Castellari, Carlo, Trombini, Claudio
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(97)00147-X