Stereospecific synthesis of aldoses based on the epoxide-opening reaction with double inversion of the configuration |
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Authors: | Hirai Atsushi Tonooka Terumichi Tanino Keiji Miyashita Masaaki |
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Affiliation: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan. |
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Abstract: | A new synthetic methodology for aldoses and aldonitols was developed in which two stereospecific epoxide-opening reactions with double inversion of the configuration, i.e., the ring-opening reaction of epoxy sulfides with phenylboronic acid and the stereospecific interconversion of trans- and cis-epoxy sulfides, were designed as the key steps. The synthetic potential of the new methodology was exemplified by the highly stereoselective synthesis of two pentose-derived sugars, arabitol and adonitol (ribitol). |
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