Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols
| Autor: | Yngve Stenstrøm, Svein Morgenlie, Dag Ekeberg |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Bromine
Hydrolysis Organic Chemistry Carbonates chemistry.chemical_element Oxidation reduction General Medicine Mass spectrometry Bridged Bicyclo Compounds Heterocyclic Biochemistry Analytical Chemistry chemistry.chemical_compound Column chromatography Sugar Alcohols chemistry Bridged Bicyclo Compounds Barium Ketoses Organic chemistry Barium carbonate Carbon Oxidation-Reduction Hexoses |
| Zdroj: | Carbohydrate research. 335(2) |
| ISSN: | 0008-6215 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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