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Stereomeric Pyrrolidinopentoses Bearing an Imidazole Ring − Synthesis, Chiroptical Properties, and Evaluation as Potential Sugar-Mimic Glycosidase Inhibitors

✍ Scribed by Théophile Tschamber; Hervé Siendt; Céline Tarnus; Dariusz Deredas; Andrzej Frankowski; Sylviane Kohler; Jacques Streith


Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
487 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis


The syntheses of the imidazolo-pyrrolidino-pentoses ent-2 (Larabino), 3 (D-xylo), 4 (D-lyxo), ent-4 (L-lyxo), and 5 (D-ribo) are reported, completing the series of all eight possible stereomers. The corresponding five linear imidazolo sugar precursors were prepared by nucleophilic addition of C(4)metallated imidazole derivatives to the appropriately configured and protected aldotetroses. Cyclisation of the resulting