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  • Title: Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols.
    Author: Ekeberg D, Morgenlie S, Stenstrøm Y.
    Journal: Carbohydr Res; 2001 Sep 28; 335(2):141-6. PubMed ID: 11567645.
    Abstract:
    A simple, but low-yielding method for the synthesis of 3-hexuloses has been elaborated. Oxidation of 1,2:5,6-di-O-isopropylidenehexitols with bromine in the presence of barium carbonate, followed by mild-acid hydrolysis of the oxidation products gave the free hexuloses. Oxidation occurred at only one of the carbon atoms bearing free hydroxyl groups. From the D-mannitol derivative, D-arabino-3-hexulose was obtained via the di-O-isopropylidene derivative, whereas the D-glucitol derivative gave a mixture of the 1,2:5,6-di-O-isoprpylidene derivatives of L-xylo- and D-ribo-3-hexulose, separable by column chromatography. Mild-acid hydrolysis of the oxidation products afforded the free hexuloses.
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