Monosaccharide Sugars book cover

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.

Audience
Chemists working in all fields of synthetic organic chemistry, biochemists interested in carbohydrate chemistry and saccharide metabolism, chemists researching isotopically labeled compounds, and medicinal chemists concerned with drug development--in general, those interested in natural products research. Also, graduate and postgraduate students in chemistry, biochemistry, and medicinal chemistry. Staff members working out laboratory procedures for undergraduate students.

Hardbound, 508 Pages

Published: December 1997

Imprint: Academic Press

ISBN: 978-0-12-550360-0

Reviews

  • "This book provides in-depth, comprehensive access to a vast body of literature on synthetic reactions involving carbohydrates. The volume is a mine of information equally useful for seeking a practical method for making a sugar-based starting material and for comprehending the influence of a controlled chiral environment on the outcome of a synthetic transformation. It is well organized by reaction type in a manner that will be readily comprehended by both the carbohydrate specialist and the general organic chemist."
    --Derek Horton, Isbell Chair of Carbohydrate Chemistry, The American University


    ...all chapters of this book are well documented with references and, therefore, provide an easy access to ample information...This book will be of benfefit to anyone who has to deal with carbohydrate chemistry."
    --Albert Levai, Department of Organic Chemistry, Kossuth Lajos University, MODELS IN CHEMISTRY 135, 1998

Contents

  • Ascending Synthesis of Monosaccharides: Building up with Total Synthesis. Building up of Sugars with Ascending Synthesis. Chain Extension with Diazoalkanes. Chain Extension with Malonester Derivatives. Chain Extensions with Phosphoranes. Olefination Reactions for the Synthesis of Chain-Extended Monosaccharides. Miscellaneous Methods for Chain Extension of the Monosaccharide Chain. Descending Synthesis of Monosaccharides: The Disulfone-Degradation. Degradation of theCalcium Salts of Aldonic Acids with Hydrogen Peroxide. Descending of Acylated Aldononitriles. Degradation of Saccharides with Oxidative Methods. Degradation of the Peroxide Derivatives of Saccharides. Chain Shortening of Saccharides by Means of Photochemical Methods. Preparation of Sugars with Isomerization: Epimerization of Saccharides in Alkaline Medium. Epimerization of Sugars with Molybdate Ions. Epimerization of Saccharides with the Amine-Complexes of Transition and Alkali-Earth Metals. Subject Index.

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