Synthesis, conformation, and glycosidic coupling reactions of highly active substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4-di-O-benzyl-α-d-xylopyranose

Yang, Guangbin; Kong, Fanzuo; Fraser, Robert R.

doi:10.1016/0008-6215(94)84074-1

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Cited by 20 publications

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The Synthesis of Imidazol Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase‐Catalysed Hydrolysis of Oligo and Polysaccharides

Streith¹,

Rudyk

Tschamber

et al. 1999

European J Organic Chem

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Some naturally occurring carbohydrates, of which several hydroxy groups had been selectively protected, were condensed with formamidine to give the expected imidazole derivatives in the D‐arabino (9), D‐lyxo (12), L‐xylo (17), D‐threo (21), and in the L‐ and D‐erythro (24) series. Introduction of a strong leaving group at the remaining free alcohol function of these products led at once to intramolecular SN2 cyclisation to the corresponding bicyclic aza sugar derivatives. This was followed by total deprotection to give the target aza sugars in the L‐xylo (7), L‐ribo (14), D‐arabino (19), as well as in the D‐threo (22) and the L‐ and D‐erythro (26) series. Inhibitory assays with four glycosidases showed that the D‐arabino aza sugar 19 is the only potent inhibitor (for an α‐mannosidase of jack bean).

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