Preparation of N-nosyl-3,4-epimines derived from levoglucosan by sodium borohydride reduction |
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| Authors: | Kroutil Jirí Karban Jindrich |
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| Affiliation: | Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, CZE-128 43 Prague 2, Czech Republic. kroutil@natur.cuni.cz |
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| Abstract: | Starting from 1,6-anhydro-beta-d-glucopyranose 1 (levoglucosan), N-o-nitrobenzenesulfonyl (nosyl) 3,4-epimino derivatives with d-allo, d-galacto, and d-talo configurations have been prepared via NaBH(4) reduction of suitably substituted azido tosylates. The benefits and limitations of this method over the classical LiAlH(4) reduction method are discussed. |
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| Keywords: | Azide reduction Stereospecific synthesis NMR spectral data Aziridines o-Nitrobenzenesulfonyl derivatives |
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