Structure and anomeric configuration of the C-nucleoside analogs obtained by dehydration of 7-deoxy-l-manno-2-heptulose phenylosazone |
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Authors: | Mohammed A.E. Sallam |
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Affiliation: | Department of Chemistry, Faculty of Science, Alexandria University, Alexandria Egypt |
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Abstract: | Dehydration of 7-deoxy-l-manno-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro-osazone derivatives (2 and 3). Refluxing the anhydro-osazones with copper sulfate gave two C-nucleoside analogs, namely, 4-(5-deoxy-α-l-arabinofuranosyl)-2-phenyl-ν-triazole (4) and 4-(5-deoxy-β-l-arabinofuranosyl)-2-phenyl-ν-triazole (5). The structure and anomeric configurations of 2, 4, and 5 were determined by n.m.r. spectroscopy. The preponderant conformation of 4 and 5, and the mass spectra of 2, 4, and 5 are discussed. |
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Keywords: | To whom enquiries should be addressed |
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