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Table of contents
- Contentsv
- Acknowledgementsxi
- Abbreviationsxiii
- Chapter 1. Introduction1
- 1. Organization of the Book1
- 1.1 Definition and Nomenclature of C-Glycosides1
- 1.2 O-Glycosides vs. C-Glycosides: Comparisons of Physical Properties, Anomeric Effects, H-Bonding A4
- 1.3 Naturally Occurring C-Glycosides7
- 1.4 C-Glycosides as Stable Pharmacophores10
- 1.5 Further Reading22
- 1.6 References22
- Chapter 2. Electrophilic Substitutions29
- 2. Introduction29
- 2.1 Anomeric Activating Groups and Stereoselectivity29
- 2.2 Cyanation Reactions30
- 2.3 Alkylation, Allenylation, Allylation and Alkynation Reactions42
- 2.4 Arylation Reactions71
- 2.5 Reactions with Enol Ethers, Silylenol Ethers and Enamines89
- 2.6 Nitroalkylation Reactions98
- 2.7 Reactions with Allylic Ethers101
- 2.8 Wittig Reactions with Lactols104
- 2.9 Nucleophilic Additions to Sugar Lactones Followed by Lactol Reductions111
- 2.10 Nucleophilic Additions to Sugars Containing Enones116
- 2.11 Transition Metal Mediated Carbon Monoxide Insertions119
- 2.12 Reactions Involving Anomeric Carbenes123
- 2.13 Reactions Involving Exoanomeric Methylenes125
- 2.14 References128
- Chapter 3. Nucleophilic Sugar Substitutions133
- 3. Introduction133
- 3.1 C1 Lithiated Anomeric Carbanions by Direct Metal Exchange134
- 3.2 C1 Lithiated Anomeric Carbanions by Reduction140
- 3.3 C1 Carbanions Stabilized by Sulfones, Sulfides, Sulfoxides, Carboxyl and Nitro Groups143
- 3.4 References152
- Chapter 4. Transition Metal Mediated C-Glycosidations155
- 4. Introduction155
- 4.1 Direct Coupling of Glycals and Aryl Groups155
- 4.2 Coupling of Substituted Glycals with Aryl Groups164
- 4.3 Coupling of Pi-Allyl Complexes of Glycals167
- 4.4 Mechanistic Considerations171
- 4.5 References173
- Chapter 5. Anomeric Radicals175
- 5. Introduction175
- 5.1 Sources of Anomeric Radicals and Stereochemical Consequences175
- 5.2 Anomeric Couplings with Radical Acceptors180
- 5.3 Intramolecular Radical Reactions192
- 5.4 References195
- Chapter 6. Rearrangements and Cycloadditions197
- 6. Introduction197
- 6.1 Rearrangements by Substituent Cleavage and Recombination198
- 6.2 Electrocyclic Rearrangements Involving Glycals201
- 6.3 Rearrangements from the 2-Hydroxyl Group204
- 6.4 Bimolecular Cycloadditions206
- 6.5 Manipulations of C-Glycosides206
- 6.6 References210
- Chapter 7. Sugar Ring Formations211
- 7. Introduction211
- 7.1 Wittig Reactions of Lactols Followed by Ring Closures212
- 7.2 Addition of Grignard and Organozinc Reagents to Lactols219
- 7.3 Cyclization of Suitably Substituted Polyols220
- 7.4 Rearrangements226
- 7.5 Cycloadditions230
- 7.6 Other Methods for the Formation of Sugar Rings233
- 7.7 References234
- Chapter 8. Syntheses of C-Di and Trisaccharides237
- 8. Introduction237
- 8.1 Syntheses Reported in 1983237
- 8.2 Syntheses Reported in 1984238
- 8.3 Syntheses Reported in 1985240
- 8.4 Syntheses Reported in 1986242
- 8.5 Syntheses Reported in 1987244
- 8.6 Syntheses Reported in 1988245
- 8.7 Syntheses Reported in 1989247
- 8.8 Syntheses Reported in 1990252
- 8.9 Syntheses Reported in 1991254
- 8.10 Syntheses Reported in 1992259
- 8.11 Syntheses Reported in 1993266
- 8.12 Syntheses Reported in 1994272
- 8.13 Trends of the Future274
- 8.14 References276
- Index279
- Authors' Biographies291
Book details
- Vendor Elsevier S & T
- SKU 9780080420806
- ISBN-13 9780080529011
Do you have questions about this book?
In recent years C-glycoside chemistry has been one of the main topics in carbohydrate chemistry, not only because of the synthetic challenges posed, but also because C-glycosides have the potential to serve as carbohydrate analogues resistant to metabolic processes. Consequently, this class of compounds is currently receiving much interest as a potential source of therapeutic agents for clinical use. This book provides a broad coverage of the various synthetic methods available for the preparation of C-glycosides, and illustrates the interesting breadth of connections between carbohydrate chemistry and modern general synthetic organic chemistry by including topics such as transition-metal catalysis, radical chemistry, cycloaddition and rearrangement processes. In addition, in the final chapter of the book, the syntheses of C-di and trisaccharides reported through 1994 are reviewed. This well organised account of the synthetic chemistry in this field will prove to be very valuable to a wide range of researchers and advanced students, both as an introduction to the topic and for reference.
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