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Synthesis and biological evaluation of the first example of an eight-membered iminoalditol |
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| Authors: | Guillaume Godin Philippe Compain Olivier R. Martin Kyoko Ikeda |
| Affiliation: | a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France b Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan |
| Abstract: | The synthesis of the first examples of eight-membered iminoalditols has been achieved from 2,3,4,6-tetra-O-benzyl-d-glucopyranose by way of a ring-closing metathesis. The (2R,3R,4R,5S)-2-hydroxymethyl-azocane-3,4,5-triol (3a), which has the d-gluco configuration for C-2-C-5 and appears to exist predominantly in a boat-chair conformation, is a weak inhibitor of glycosidases. |
| Keywords: | Iminoalditols Azocanes Glycosidase inhibitors |
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