Cyclic acetals of ketoses : Part IV. Re-investigation of the oxidation of 1,2:4,5-DI-O-isopropylidene-β-D-fructopyranose with methyl sulfoxide—acetic anhydride
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Add time:08/31/2019 Source:sciencedirect.com
For the preparation of pure D-psicose (5a) via oxidation of 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose (2a), the latter must be free from its 2,3:4,5 isomer (6a), which is oxidized to the corresponding aldosulose acetal. Pure 1,2:4,5-di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose (3) undergoes stereospecific reduction with sodium borohydride to give only 1,2:4,5-di-O-isopropylidene-β-D-ribo-hexulopyranose (4a), which exists as two different crystal modifications. Compounds 3 and 4a have been characterized, and discrepancies in the literature have been explained.
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