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C-Furanosides

Synthesis and Stereochemistry

  • 1st Edition - November 30, 2017
  • Latest edition
  • Authors: Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier
  • Language: English

Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological ap… Read more

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Description

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.

Key features

  • 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target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases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

Readership

Organic, natural product, and carbohydrate chemists in industry and academia

Table 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

Product details

  • Edition: 1
  • Latest edition
  • Published: November 30, 2017
  • Language: English

About the authors

PG

Peter Goekjian

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.
Affiliations and expertise
Chemistry Department, Claude Bernard University Lyon 1, Lyon, France

AH

Arnaud Haudrechy

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.
Affiliations and expertise
Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France

BM

Boudjema Menhour

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.
Affiliations and expertise
Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France

CC

Claire Coiffier

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.
Affiliations and expertise
Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France

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