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Author Goekjian, Peter, author.

Title C-furanosides : synthesis and stereochemistry / Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier.

Publication Info. London, United Kingdom : Academic Press, an imprint of Elsevier, [2018]

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 Axe Elsevier ScienceDirect Ebook  Electronic Book    ---  Available
Description 1 online resource
text txt rdacontent
computer c rdamedia
online resource cr rdacarrier
Bibliography Includes bibliographical references and index.
Note Online resource; title from PDF title page (Ebsco, viewed December 12, 2017).
Summary 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.
Contents Machine generated contents note: -- pt. A C-Glycosides of Lyxose and Ribose: galacto-, altro- and alio- Configurations -- A. Introduction -- References -- A.1. galacto-C-Furanosides (I, ╬▓-C-Lyxose) -- Disconnections -- Natural Occurrence -- A.1.1. Disconnection A -- A.1.2. Disconnection B -- A.1.3. Disconnection C -- A.1.4. Disconnection D -- A.1.5. Miscellaneous -- A.1.6. Conclusion -- References -- A.2. D- and L-altro-C-furanosides (II/ent-II, ╬-C-Lyxose, ╬-C-Ribose) -- Disconnections -- Natural Occurrence -- A.2.1. Disconnection A -- A.2.2. Disconnection B -- A.2.3. Disconnection C -- A.2.4. Disconnection D -- A.2.5. Disconnection E -- A.2.6. Miscellaneous -- A.2.7. Conclusion -- References -- A.3. allo-C-Furanosides (VI, ╬▓-C-Ribose) Disconnections -- Natural Occurrence -- A.3.1. Disconnection A -- A.3.2. Disconnection B -- A.3.3. Disconnection C -- A.3.4. Disconnection D -- A.3.5. Disconnection E -- A.3.6. Miscellaneous -- A.3.7. Conclusion -- References -- A.4. Lyxose and Ribose C-Glycosides: Other Results and Further Insight Into Stereochemistry -- A.4.1. Disconnection A -- A.4.2. Disconnection B -- A.4.3. Disconnection C -- A.4.4. Disconnection D -- A.4.5. Miscellaneous -- A.4.6. Conclusion -- References -- pt. B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations -- B. Introduction -- References -- B.1. Gluco-C-Furanosides (III/ent-III, ╬▓-C-Arabinose, ╬▓-C-Xylose) Disconnections -- Natural Occurrence -- B.1.1. Disconnection A -- B.1.2. Disconnection B -- B.1.3. Disconnection C -- B.1.4. Disconnection D -- B.1.5. Miscellaneous -- B.1.6. Conclusion -- References -- B.2. ido-C-Furanosides (V/ent-V, ╬-C-Xylose) Disconnections -- Natural Occurrences -- B.2.1. Disconnection A -- B.2.2. Disconnection B -- B.2.3. Disconnection C -- B.2.4. Disconnection D -- B.2.5. Miscellaneous -- B.2.6. Conclusion -- References -- B.3. manno-C-Furanosides (VII/ent-VII, ╬-C-Arabinose) Disconnections -- Natural Occurrence -- B.3.1. Disconnection A -- B.3.2. Disconnection B -- B.3.3. Disconnection C -- B.3.4. Disconnection D -- B.3.5. Conclusion -- References -- B.4. Arabinose and Xylose C-Furanosides: Other Results and Further Insight Into Stereochemistry Disconnections -- B.4.1. Disconnection A -- B.4.2. Disconnection B -- B.4.3. Disconnection C -- B.4.4. Equilibration Processes -- B.4.5. Miscellaneous -- B.4.6. Conclusion -- References -- pt. 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 -- References -- pt. D. 1H NMR Vicinal Coupling Constants of C-Furanosides -- Introduction -- D.1. 1H NMR Data in galacto-C-Furanosides (I, ╬▓-C-Lyxose), Corresponding to Chapter A.1 -- D.2. 1H NMR Data in D- and L-altro-C-Furanosides (II/ent-II, ╬-C-Lyxose, ╬-C-Ribose), Corresponding to Chapter A.2 -- D.3. Comparison Between 1H NMR Data in galacto-C- Furanosides (I, ╬▓-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-altro-C-Furanosides (II/ent-II, ╬-C-Lyxose, ╬-C-Ribose), Corresponding to Chapter A.2 -- D.4. 1H NMR Data in allo-C-Furanosides (VI, ╬▓-C-Ribose), Corresponding to Chapter A.3 -- D.5. Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, ╬-C-Lyxose, ╬-C-Ribose), Corresponding to Chapter A.2, and in allo-C-Furanosides (VI, ╬▓-C-Ribose), Corresponding to Chapter A.3 -- D.6. 1H NMR Data in D- and L-gluco-C-Furanosides (III/ent-III, ╬▓-C-Arabinose, ╬▓-C-Xylose), Corresponding to Chapter B.1 -- D.7. 1H NMR Data in D- and L-ido-C-Furanosides (V/ent-V, ╬-C-D-Xylose, ╬-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, ╬▓-C-Arabinose, ╬▓-C-Xylose), Corresponding to Chapter B.1, and in D- and L-ido-C-Furanosides (V/ent-V, ╬-C-D-Xylose, ╬-C-L-Xylose), Corresponding to Chapter B.2 -- D.9. 1H NMR Data in D- and L-manno-C-Furanosides (VII/ent-VII, ╬-C-Arabinose), Corresponding to Chapter B.3 -- D.10. Comparison Between 1H NMR Data in galacto-C- Furanosides (I, ╬▓-C-Lyxose), Corresponding to Chapter A.1, and in D- and L-gluco-C-Furanosides (III/ent-III, ╬▓-C-Arabinose, ╬▓-C-Xylose), Corresponding to Chapter B.1 -- D.11. Comparison Between 1H NMR Data in D- and L-altro- C-Furanosides (II/ent-II, ╬-C-Lyxose, ╬-C-Ribose), Corresponding to Chapter A.2, and in D- and L-ido- C-Furanosides (V/ent-V, ╬-C-D-Xylose, ╬-C-L-Xylose), Corresponding to Chapter B.2 -- D.12. Conclusion and Summary of Expected Coupling Constants -- References.
Subject Diastereoisomers.
DiastÚrÚo-isomŔres.
SCIENCE -- Chemistry -- Organic.
Diastereoisomers. (OCoLC)fst00892725
Added Author Hauchy, Arnaud, author.
Menhour, Boudjema, author.
Coiffier, Claire, author.
Other Form: Print version: Goekjian, Peter. C-furanosides. London, United Kingdom : Academic Press, an imprint of Elsevier, [2018] (DLC) 2017960866
ISBN 9780128037898 (electronic bk.)
012803789X (electronic bk.)
9780128037393
0128037393 (paperback)
9780128037393
Standard No. AU@ 000061503018
AU@ 000066136147

 
    
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