Monosaccharide Sugars: Chemical Synthesis by Chain Elongation, Degradation, and Epimerization
In a single volume, Monosaccharide Sugars critically summarizes the applied and potentially useful strategies for the synthesis and degradation of monosaccharides by chain-elongation, degradation, and epimerization. These methodologies permit the synthesis of rare or unnatural monosaccharides that are frequently employed as chiral building blocks in natural products synthesis, as well as for producing sugar derivatives labeled with radioactive isotopes. Representative and well-established experimental procedures are provided to illustrate the potential of the synthetic transformation.Degradation of carbohydrates also represents an invaluable tool for the structural elucidation of certain natural products, suchas glycosides, antibiotics, and polysaccharides. When describing the individual methods, unique supplementary collections of the prepared sugar derivatives are shown in tabular form. This compendium will eliminate tedious literature searches for those engaged in research and teaching on the chemistry and biochemistry of saccharides and other natural products, and also for those working on the medicinal and metabolic investigation of related substances of biological importance.
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acid Acta added dropwise addition aldehydo-sugars aldol aldose anomeric aqueous NaHCO3 benzene bromide Carbohydr carbon CH.OH chain extension CHCl3 Chem Chim chloride chloroform column chromatography column chromatography eluant compounds concentrated condensation cooled crystals D-arabinose degradation derivatives dichloromethane dissolved distilled dithioacetal dry THF Educt epimerization ester ether ethyl acetate evaporated extracted filtered filtrate glycals H.C. CH Helv hexane Justus Liebigs Justus Liebigs Ann Khim lactone lead tetraacetate methanol methyl mixture is stirred mmol monosaccharides n-butyllithium OAC ACO OAC OAC OAC OBn OBn obtained OH OH OH olefination organic layer oxidation Perkin Trans Phosphorane preparation procedure pyridine reaction mixture reagent recrystallized Ref(s reflux residue resin room temperature saccharide saturated aqueous shown in Figure silicagel sodium solution solvent sugar synthesis syrup Tetrahedron Lett transformation washed with water yield
Page 30 - RG Ault, DK Baird, HC Carrington, WN Haworth, R. Herbert, EL Hirst, EGV Percival, F. Smith, and M. Stacey, J. Chem. Soc., p.