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C-Furanosides

  • ID: 3980563
  • Book
  • November 2017
  • Region: Global
  • 794 Pages
  • Elsevier Science and Technology
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Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological applications, as conformational probes, or for biological studies. C-Furanosides: Synthesis and Stereochemistry provides a much-needed overview of synthetic and stereochemical principles for C-furanosides: analogs of a 5-membered ring carbohydrate glycoside (furanoside), in which the anomeric oxygen has been replaced with a carbon.

While our understanding of conformational behavior and of stereoselective synthesis in 6-membered ring compounds is quite good, our ability to predict the conformation of 5-membered ring compounds, or to predict the stereochemical outcome of a given reaction, remains anecdotal. Through a comprehensive review of literature approaches to the different C-furanoside stereoisomers, as well as an interpretation of the outcome in terms of a reasonable number of stereochemical models, C-Furanosides: Synthesis and Stereochemistry enables the reader to determine the best approach to a particular C-glycoside compound, and also hopes to provide a certain level of rationalization and predictability for the synthesis of new systems.

  • Provides a comprehensive review of the growing literature in C-furanosides
  • Enables readers to choose the most convenient approach to access a defined target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases
  • Explores the various rational models for stereochemical analysis of furanoside reactivity, with a clear distinction made between physical chemical mechanisms and stereochemical models

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The Stereochemistry of C-Furanosides  Part A. C-Glycosides of Lyxose and Ribose: galacto-, altro- and allo- Configurations A. Introduction A.1. galacto-C-Furanosides (I, b-C-Lyxose) A.2. D- and  L-altro-C-furanosides (II/ent-II,  a-C-Lyxose, a-C-Ribose) A.3. allo-C-Furanosides (VI, b-C-Ribose) A.4. Lyxose and  Ribose C-Glycosides: Other Results and  Further  Insight Into  Stereochemistry Part B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations B. Introduction B.1. Gluco-C-Furanosides (III/ent-III,  b-C-Arabinose, b-C-Xylose) B.2. ido-C-Furanosides (V/ent-V, a-C-Xylose) B.3. manno-C-Furanosides (VII/ent-VII, a-C-Arabinose) B.4. Arabinose and  Xylose C-Furanosides: Other Results and  Further  Insight Into  Stereochemistry Part C. Applications of C-Furanosides Introduction C.1. Preparation of C-Furanosides   C.2. Agro-Industry and  Farming   C.3. Ligands for Asymmetric  Catalysis   C.4. Perfumes, Aromas,  and  Cosmetics   C.5. Imaging  and  Diagnostics C.6. Pharmaceutical Industry   C.7. Polymers Part D. 1H NMR Vicinal Coupling Constants of C-Furanosides Introduction   D.1. 1H NMR Data  in galacto-C-Furanosides (I, b-C-Lyxose), Corresponding to Chapter A.1  D.2. 1H NMR Data  in D- and  L-altro-C-Furanosides (II/ent-II, a-C-Lyxose,  a-C-Ribose), Corresponding to Chapter A.2  D.3. Comparison Between 1H NMR Data  in galacto-C-Furanosides (I, b-C-Lyxose),  Corresponding to Chapter A.1, and  in D- and  L-altro-C-Furanosides (II/ent-II,  a-C-Lyxose,  a-C-Ribose), Corresponding to Chapter A.2  D.4. 1H NMR Data  in allo-C-Furanosides (VI, b-C-Ribose), Corresponding to Chapter A.3  D.5. Comparison Between 1H NMR Data  in D- and  L-altro-C-Furanosides (II/ent-II,  a-C-Lyxose,  a-C-Ribose), Corresponding to Chapter A.2, and  in allo-C-Furanosides (VI, b-C-Ribose), Corresponding to Chapter A.3  D.6. 1H NMR Data  in D- and  L-gluco-C-Furanosides (III/ent-III,  b-C-Arabinose, b-C-Xylose),  Corresponding to Chapter B.1  D.7/ 1H NMR Data  in D- and  L-ido-C-Furanosides (V/ent-V, a-C-D-Xylose, a-C-L-Xylose),  Corresponding to Chapter B.2  D.8. Comparison Between 1H NMR Data  in D- and  L-gluco- C-Furanosides (III/ent-III,  b-C-Arabinose, b-C-Xylose), Corresponding to Chapter B.1, and  in D- and  L-ido-C-Furanosides (V/ent-V, a-C-D-Xylose, a-C-L-Xylose), Corresponding to Chapter B.2  D.9. 1H NMR Data  in D- and  L-manno-C-Furanosides(VII/ent-VII, a-C-Arabinose), Corresponding to Chapter B.3  D.10. Comparison Between 1H NMR Data  in galacto-C-Furanosides (I, b-C-Lyxose),  Corresponding to Chapter A.1, and  in D- and  L-gluco-C-Furanosides (III/ent-III, b-C-Arabinose, b-C-Xylose),  Corresponding to Chapter B.1  D.11  Comparison Between 1H NMR Data  in D- and  L-altro- C-Furanosides (II/ent-II,  a-C-Lyxose, a-C-Ribose), Corresponding to Chapter A.2, and  in D- and  L-ido- C-Furanosides (V/ent-V, a-C-D-Xylose, a-C-L-Xylose), Corresponding to Chapter B.2  D.12. Conclusion and  Summary  of Expected Coupling Constants  

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Goekjian, Peter
Dr. Peter Goekjian has been Professor of Chemistry at Université Claude Bernard-Lyon 1, France, since September 2000. His research interests are carbohydrate chemistry, total synthesis of glycosidic natural products, targeted methodology, and the role of glycosylation in signal transduction and gene expression. He was involved in the early work on the use of C-glycosides as conformational probes in the late 1980s and early 1990s.
Haudrechy, Arnaud
Dr. Arnaud Haudrechy has been a Professor of Chemistry at the Université of Reims Champagne Ardenne, France, since September 2003. His research interests include carbohydrate chemistry, total synthesis of natural substances, development of methodologies, and didactical techniques. He was involved in the early work on the use of C-glycosides as conformational probes in the late 1980s and early 1990s.
Menhour, Boudjema
Dr. Boudjema Menhour has a PhD in Organic Chemistry and is a researcher at the Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France. He research interests include developing a synthesis of carbohydrate analogues, targeting a specific activity, such as immunostimulatory, and eliciting properties.
Coiffier, Claire
Claire Coiffier, PhD, is a researcher at the Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France. She has worked on the top-down approach for the synthesis of biologically active substrates and on the analysis of preferred conformations of C-furanosides, using theoretical chemistry.
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