C-Furanosides - Synthesis and Stereochemistry

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.

List of contents

The Stereochemistry of C-Furanosides Part A. C-Glycosides of Lyxose and Ribose: galacto-, altro- and allo- ConfigurationsA. IntroductionA.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 StereochemistryPart B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- ConfigurationsB. IntroductionB.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 StereochemistryPart C. Applications of C-FuranosidesIntroduction 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-FuranosidesIntroduction 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 toChapter 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

About the author

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.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.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.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.

Product details

• Authors: Claire Coiffier, Coiffier Claire, Peter Goekjian, Goekjian Peter, Arnaud Haudrechy, Haudrechy Arnaud, Boudjema Menhour, Menhour Boudjema
• Publisher: Elsevier Science & Technology
• Languages: English
• Product format: Paperback / Softback
• Released: 30.11.2017
• EAN: 9780128037393
• ISBN: 978-0-12-803739-3
• Dimensions: 152 mm x 36 mm x 229 mm
• Weight: 1250 g
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; ORGANIC CHEMISTRY, SCIENCE / Chemistry / General, SCIENCE / Chemistry / Organic, chemistry