- Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols.
Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols.
Carbohydrate research (2001-09-25)
D Ekeberg, S Morgenlie, Y Stenstrøm
PMID11567645
RESUMEN
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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