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C-Furanosides
Synthesis and Stereochemistry
Comprehensive overview that examines published approaches to different C-furanoside stereoisomers and interprets outcomes in a number of stereochemical models
Peter Goekjian (Author), Arnaud Haudrechy (Author), Boudjema Menhour (Author), Claire Coiffier (Author)
9780128037393, Elsevier Science
Paperback, published 30 November 2017
794 pages
22.9 x 15.1 x 4.8 cm, 1.25 kg
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.
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
