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.

Provides a comprehensive review of the growing literature in C-furanosidesEnables 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target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished casesExplores the various rational models for stereochemical analysis of furanoside reactivity, with a clear distinction made between physical chemical mechanisms and stereochemical models

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