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Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols. 2001

D Ekeberg, and S Morgenlie, and Y Stenstrøm
Department of Chemistry and Biotechnology, Section Chemistry, Agricultural University of Norway, PO Box 5040, N-1432 As, Norway.

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.

UI MeSH Term Description Entries
D007661 Ketoses MONOSACCHARIDES containing one ketone group per molecule. Keto Sugar,Keto Sugars,Ketose,Sugar, Keto,Sugars, Keto
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D001966 Bromine A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested. Bromine-79,Bromine 79
D002254 Carbonates Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed) Carbonate
D006601 Hexoses MONOSACCHARIDES whose molecules contain six carbon atoms, such as GLUCOSE and FRUCTOSE. They generally have the chemical formula C6H12O6. Hexose
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D001464 Barium An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.
D013402 Sugar Alcohols Polyhydric alcohols having no more than one hydroxy group attached to each carbon atom. They are formed by the reduction of the carbonyl group of a sugar to a hydroxyl group. (From Dorland, 28th ed) Alcohols, Sugar,Alditol,Sugar Alcohol,Alditols,Alcohol, Sugar
D019086 Bridged Bicyclo Compounds, Heterocyclic Heterocyclic compounds that contain two rings that share two non-adjacent atoms in common. Bicyclo Compounds, Heterocyclic,Heterocyclic Cpds, Bicyclic,Bicyclic Heterocyclic Compounds,Heterocyclic Bicyclo Compounds,Bicyclic Heterocyclic Cpds,Heterocyclic Compounds, Bicyclic

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