Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide |
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Authors: | Vrushali H. Jadhav Omprakash P. Bande Vedavati G. Puranik Dilip D. Dhavale |
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Affiliation: | 1. Department of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India;2. Centre for Material Characterization, National Chemical Laboratory, Pune 411 008, India |
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Abstract: | The Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol 4 afforded α- and β-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido diol 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. |
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