General access to iminosugar C-glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics |
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Authors: | Godin Guillaume Compain Philippe Martin Olivier R |
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Institution: | Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d'Orléans, rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France. |
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Abstract: | reaction: see text] Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest. |
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