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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-...
| Clasificación: | Libro Electrónico |
|---|---|
| Autores principales: | , , , |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
London, United Kingdom :
Academic Press, an imprint of Elsevier,
[2018]
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| Temas: | |
| Acceso en línea: | Texto completo |
MARC
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| 100 | 1 | |a Goekjian, Peter, |e author. | |
| 245 | 1 | 0 | |a C-furanosides : |b synthesis and stereochemistry / |c Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier. |
| 264 | 1 | |a London, United Kingdom : |b Academic Press, an imprint of Elsevier, |c [2018] | |
| 300 | |a 1 online resource | ||
| 336 | |a text |b txt |2 rdacontent | ||
| 337 | |a computer |b c |2 rdamedia | ||
| 338 | |a online resource |b cr |2 rdacarrier | ||
| 504 | |a Includes bibliographical references and index. | ||
| 588 | 0 | |a Online resource; title from PDF title page (Ebsco, viewed December 12, 2017). | |
| 520 | |a 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. | ||
| 505 | 0 | 0 | |g Machine generated contents note: -- |g pt. |t A C-Glycosides of Lyxose and Ribose: galacto-, altro- and alio- Configurations -- |g A. |t Introduction -- |t References -- |g A.1. |t galacto-C-Furanosides (I, �I²-C-Lyxose) -- |t Disconnections -- |t Natural Occurrence -- |g A.1.1. |t Disconnection A -- |g A.1.2. |t Disconnection B -- |g A.1.3. |t Disconnection C -- |g A.1.4. |t Disconnection D -- |g A.1.5. |t Miscellaneous -- |g A.1.6. |t Conclusion -- |t References -- |g A.2. |t D- and L-altro-C-furanosides (II/ent-II, �I�-C-Lyxose, �I�-C-Ribose) -- |t Disconnections -- |t Natural Occurrence -- |g A.2.1. |t Disconnection A -- |g A.2.2. |t Disconnection B -- |g A.2.3. |t Disconnection C -- |g A.2.4. |t Disconnection D -- |g A.2.5. |t Disconnection E -- |g A.2.6. |t Miscellaneous -- |g A.2.7. |t Conclusion -- |t References -- |g A.3. |t allo-C-Furanosides (VI, �I²-C-Ribose) Disconnections -- |t Natural Occurrence -- |g A.3.1. |t Disconnection A -- |g A.3.2. |t Disconnection B -- |g A.3.3. |t Disconnection C -- |g A.3.4. |t Disconnection D -- |g A.3.5. |t Disconnection E -- |g A.3.6. |t Miscellaneous -- |g A.3.7. |t Conclusion -- |t References -- |g A.4. |t Lyxose and Ribose C-Glycosides: Other Results and Further Insight Into Stereochemistry -- |g A.4.1. |t Disconnection A -- |g A.4.2. |t Disconnection B -- |g A.4.3. |t Disconnection C -- |g A.4.4. |t Disconnection D -- |g A.4.5. |t Miscellaneous -- |g A.4.6. |t Conclusion -- |t References -- |g pt. B. |t C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations -- |g B. |t Introduction -- |t References -- |g B.1. |t Gluco-C-Furanosides (III/ent-III, �I²-C-Arabinose, �I²-C-Xylose) Disconnections -- |t Natural Occurrence -- |g B.1.1. |t Disconnection A -- |g B.1.2. |t Disconnection B -- |g B.1.3. |t Disconnection C -- |g B.1.4. |t Disconnection D -- |g B.1.5. |t Miscellaneous -- |g B.1.6. |t Conclusion -- |t References -- |g B.2. |t ido-C-Furanosides (V/ent-V, �I�-C-Xylose) Disconnections -- |t Natural Occurrences -- |g B.2.1. |t Disconnection A -- |g B.2.2. |t Disconnection B -- |g B.2.3. |t Disconnection C -- |g B.2.4. |t Disconnection D -- |g B.2.5. |t Miscellaneous -- |g B.2.6. |t Conclusion -- |t References -- |g B.3. |t manno-C-Furanosides (VII/ent-VII, �I�-C-Arabinose) Disconnections -- |t Natural Occurrence -- |g B.3.1. |t Disconnection A -- |g B.3.2. |t Disconnection B -- |g B.3.3. |t Disconnection C -- |g B.3.4. |t Disconnection D -- |g B.3.5. |t Conclusion -- |t References -- |g B.4. |t Arabinose and Xylose C-Furanosides: Other Results and Further Insight Into Stereochemistry Disconnections -- |g B.4.1. |t Disconnection A -- |g B.4.2. |t Disconnection B -- |g B.4.3. |t Disconnection C -- |g B.4.4. |t Equilibration Processes -- |g B.4.5. |t Miscellaneous -- |g B.4.6. |t Conclusion -- |t References -- |g pt. C. |t Applications of C-Furanosides Introduction -- |g C.1. |t Preparation of C-Furanosides -- |g C.2. |t Agro-Industry and Farming -- |g C.3. |t Ligands for Asymmetric Catalysis -- |g C.4. |t Perfumes, Aromas, and Cosmetics -- |g C.5. |t Imaging and Diagnostics -- |g C.6. |t Pharmaceutical Industry -- |g C.7. |t Polymers -- |t References -- |g pt. D. |t 1H NMR Vicinal Coupling Constants of C-Furanosides -- |t Introduction -- |g D.1. |t 1H NMR Data in galacto-C-Furanosides (I, �I²-C-Lyxose), Corresponding to Chapter A.1 -- |g D.2. |t 1H NMR Data in D- and L-altro-C-Furanosides (II/ent-II, �I�-C-Lyxose, �I�-C-Ribose), Corresponding to Chapter A.2 -- |g D.3. |t Comparison Between 1H NMR Data in galacto-C- Furanosides (I, �I²-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-altro-C-Furanosides (II/ent-II, �I�-C-Lyxose, �I�-C-Ribose), Corresponding to Chapter A.2 -- |g D.4. |t 1H NMR Data in allo-C-Furanosides (VI, �I²-C-Ribose), Corresponding to Chapter A.3 -- |g D.5. |t Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, �I�-C-Lyxose, �I�-C-Ribose), Corresponding to Chapter A.2, and in allo-C-Furanosides (VI, �I²-C-Ribose), Corresponding to Chapter A.3 -- |g D.6. |t 1H NMR Data in D- and L-gluco-C-Furanosides (III/ent-III, �I²-C-Arabinose, �I²-C-Xylose), Corresponding to Chapter B.1 -- |g D.7. |t 1H NMR Data in D- and L-ido-C-Furanosides (V/ent-V, �I�-C-D-Xylose, �I�-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.8. |t Comparison Between 1H NMR Data in D- and L-gluco- C-Furanosides (III/ent-III, �I²-C-Arabinose, �I²-C-Xylose), Corresponding to Chapter B.1, and in D- and L-ido-C-Furanosides (V/ent-V, �I�-C-D-Xylose, �I�-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.9. |t 1H NMR Data in D- and L-manno-C-Furanosides (VII/ent-VII, �I�-C-Arabinose), Corresponding to Chapter B.3 -- |g D.10. |t Comparison Between 1H NMR Data in galacto-C- Furanosides (I, �I²-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-gluco-C-Furanosides (III/ent-III, �I²-C-Arabinose, �I²-C-Xylose), Corresponding to Chapter B.1 -- |g D.11. |t Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, �I�-C-Lyxose, �I�-C-Ribose), Corresponding to Chapter A.2, and in D- and L-ido- C-Furanosides (V/ent-V, �I�-C-D-Xylose, �I�-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.12. |t Conclusion and Summary of Expected Coupling Constants -- |t References. |
| 650 | 0 | |a Diastereoisomers. | |
| 650 | 6 | |a Diast�er�eo-isom�eres. |0 (CaQQLa)201-0359732 | |
| 650 | 7 | |a SCIENCE |x Chemistry |x Organic. |2 bisacsh | |
| 650 | 7 | |a Diastereoisomers |2 fast |0 (OCoLC)fst00892725 | |
| 700 | 1 | |a Hauchy, Arnaud, |e author. | |
| 700 | 1 | |a Menhour, Boudjema, |e author. | |
| 700 | 1 | |a Coiffier, Claire, |e author. | |
| 776 | 0 | 8 | |i Print version: |a Goekjian, Peter. |t C-furanosides. |d London, United Kingdom : Academic Press, an imprint of Elsevier, [2018] |w (DLC) 2017960866 |
| 856 | 4 | 0 | |u https://sciencedirect.uam.elogim.com/science/book/9780128037393 |z Texto completo |
| 880 | 0 | 0 | |6 505-00/(S |g Machine generated contents note: |g pt. |t A C-Glycosides of Lyxose and Ribose: galacto-, altro- and alio- Configurations -- |g A. |t Introduction -- |t References -- |g A.1. |t galacto-C-Furanosides (I, β-C-Lyxose) -- |t Disconnections -- |t Natural Occurrence -- |g A.1.1. |t Disconnection A -- |g A.1.2. |t Disconnection B -- |g A.1.3. |t Disconnection C -- |g A.1.4. |t Disconnection D -- |g A.1.5. |t Miscellaneous -- |g A.1.6. |t Conclusion -- |t References -- |g A.2. |t D- and L-altro-C-furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose) -- |t Disconnections -- |t Natural Occurrence -- |g A.2.1. |t Disconnection A -- |g A.2.2. |t Disconnection B -- |g A.2.3. |t Disconnection C -- |g A.2.4. |t Disconnection D -- |g A.2.5. |t Disconnection E -- |g A.2.6. |t Miscellaneous -- |g A.2.7. |t Conclusion -- |t References -- |g A.3. |t allo-C-Furanosides (VI, β-C-Ribose) Disconnections -- |t Natural Occurrence -- |g A.3.1. |t Disconnection A -- |g A.3.2. |t Disconnection B -- |g A.3.3. |t Disconnection C -- |g A.3.4. |t Disconnection D -- |g A.3.5. |t Disconnection E -- |g A.3.6. |t Miscellaneous -- |g A.3.7. |t Conclusion -- |t References -- |g A.4. |t Lyxose and Ribose C-Glycosides: Other Results and Further Insight Into Stereochemistry -- |g A.4.1. |t Disconnection A -- |g A.4.2. |t Disconnection B -- |g A.4.3. |t Disconnection C -- |g A.4.4. |t Disconnection D -- |g A.4.5. |t Miscellaneous -- |g A.4.6. |t Conclusion -- |t References -- |g pt. B |t C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations -- |g B. |t Introduction -- |t References -- |g B.1. |t Gluco-C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose) Disconnections -- |t Natural Occurrence -- |g B.1.1. |t Disconnection A -- |g B.1.2. |t Disconnection B -- |g B.1.3. |t Disconnection C -- |g B.1.4. |t Disconnection D -- |g B.1.5. |t Miscellaneous -- |g B.1.6. |t Conclusion -- |t References -- |g B.2. |t ido-C-Furanosides (V/ent-V, α-C-Xylose) Disconnections -- |t Natural Occurrences -- |g B.2.1. |t Disconnection A -- |g B.2.2. |t Disconnection B -- |g B.2.3. |t Disconnection C -- |g B.2.4. |t Disconnection D -- |g B.2.5. |t Miscellaneous -- |g B.2.6. |t Conclusion -- |t References -- |g B.3. |t manno-C-Furanosides (VII/ent-VII, α-C-Arabinose) Disconnections -- |t Natural Occurrence -- |g B.3.1. |t Disconnection A -- |g B.3.2. |t Disconnection B -- |g B.3.3. |t Disconnection C -- |g B.3.4. |t Disconnection D -- |g B.3.5. |t Conclusion -- |t References -- |g B.4. |t Arabinose and Xylose C-Furanosides: Other Results and Further Insight Into Stereochemistry Disconnections -- |g B.4.1. |t Disconnection A -- |g B.4.2. |t Disconnection B -- |g B.4.3. |t Disconnection C -- |g B.4.4. |t Equilibration Processes -- |g B.4.5. |t Miscellaneous -- |g B.4.6. |t Conclusion -- |t References -- |g pt. C |t Applications of C-Furanosides Introduction -- |g C.1. |t Preparation of C-Furanosides -- |g C.2. |t Agro-Industry and Farming -- |g C.3. |t Ligands for Asymmetric Catalysis -- |g C.4. |t Perfumes, Aromas, and Cosmetics -- |g C.5. |t Imaging and Diagnostics -- |g C.6. |t Pharmaceutical Industry -- |g C.7. |t Polymers -- |t References -- |g pt. D |t 1H NMR Vicinal Coupling Constants of C-Furanosides -- |t Introduction -- |g D.1. |t 1H NMR Data in galacto-C-Furanosides (I, β-C-Lyxose), Corresponding to Chapter A.1 -- |g D.2. |t 1H NMR Data in D- and L-altro-C-Furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose), Corresponding to Chapter A.2 -- |g D.3. |t Comparison Between 1H NMR Data in galacto-C- Furanosides (I, β-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-altro-C-Furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose), Corresponding to Chapter A.2 -- |g D.4. |t 1H NMR Data in allo-C-Furanosides (VI, β-C-Ribose), Corresponding to Chapter A.3 -- |g D.5. |t Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose), Corresponding to Chapter A.2, and in allo-C-Furanosides (VI, β-C-Ribose), Corresponding to Chapter A.3 -- |g D.6. |t 1H NMR Data in D- and L-gluco-C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose), Corresponding to Chapter B.1 -- |g D.7. |t 1H NMR Data in D- and L-ido-C-Furanosides (V/ent-V, α-C-D-Xylose, α-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.8. |t Comparison Between 1H NMR Data in D- and L-gluco- C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose), Corresponding to Chapter B.1, and in D- and L-ido-C-Furanosides (V/ent-V, α-C-D-Xylose, α-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.9. |t 1H NMR Data in D- and L-manno-C-Furanosides (VII/ent-VII, α-C-Arabinose), Corresponding to Chapter B.3 -- |g D.10. |t Comparison Between 1H NMR Data in galacto-C- Furanosides (I, β-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-gluco-C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose), Corresponding to Chapter B.1 -- |g D.11. |t Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose), Corresponding to Chapter A.2, and in D- and L-ido- C-Furanosides (V/ent-V, α-C-D-Xylose, α-C-L-Xylose), Corresponding to Chapter B.2 -- |g D.12. |t Conclusion and Summary of Expected Coupling Constants -- |t References. |