Carbohydrates
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Table of contents
- Contentsxi
- Chapter 1. An Introduction to Carbohydrate Synthesis1
- 1.1 Biological roles of carbohydrates1
- 1.2 Synthesis of carbohydrates5
- References7
- Chapter 2. Selective Hydroxyl Protection and Deprotection9
- 2.1 Introduction9
- 2.2 Hydroxyl group reactivity10
- 2.3 Ethers11
- 2.4 Esters22
- 2.5 Carbonates28
- 2.6 Acetals29
- 2.7 Experimental procedures33
- References67
- Chapter 3. Synthesis and Activation of Carbohydrate Donors: Acetates, Halides, Phenyl selenides and69
- 3.1 Introduction69
- 3.2 Acetates69
- 3.3 Halides76
- 3.4 Phenyl selenides95
- 3.5 Glycals109
- References118
- Chapter 4. Synthesis and Activation of Carbohydrate Donors: Thioglycosides and Sulfoxides121
- 4.1 Introduction121
- 4.2 Thioglycosides121
- 4.3 Sulfoxides137
- References142
- Chapter 5. Synthesis and Activation of Carbohydrate Donors: Acetimidates, n-Pentenyl and Vinyl Glyco147
- 5.1 The trichloroacetimidate method148
- 5.2 Use of n-pentenyl glycosides as glycosyl donors165
- 5.3 Use of vinyl glycosides as glycosyl donors181
- 5.4 Overall summary191
- References192
- Chapter 6. Modern Glycosidation Methods: Tuning of Reactivity195
- 6.1 Introduction195
- 6.2 Influence of protecting groups197
- 6.3 Influence of leaving group205
- 6.4 Summary211
- References216
- Chapter 7. Modern Glycosidation Methods: Orthogonal Glycosidation219
- 7.1 Introduction219
- 7.2 Orthogonal glycosidations220
- References237
- Chapter 8. The Stereoselective Synthesis of β-Mannosides239
- 8.1 The natural occurrence of β-mannosides239
- 8.2 Problems associated with β-mannoside synthesis241
- 8.3 Synthetic methods242
- 8.4 Conclusion274
- References274
- Chapter 9. Synthesis of Sialic Acid Containing Carbohydrates277
- 9.1 Introduction277
- 9.2 Sialic acid donors278
- 9.3 Sialylation in oligosaccharide synthesis289
- References305
- Chapter 10. The Synthesis of Glycosyl Amino Acids311
- 10.1 Introduction311
- 10.2 O-Glycosylamino acids and O-glycopeptides311
- 10.3 N-Glycosylamino acids and N-glycopeptides317
- 10.4 Solid phase synthesis of N- and O-glycosylamino acids and N- and O-glycopeptides322
- 10.5 Conclusion323
- 10.6 Experimental procedures323
- References333
- Chapter 11. The Synthesis of C-linked Glycosides337
- 11.1 Introduction337
- 11.2 Synthetic methods339
- 11.3 Conclusion381
- References381
- Chapter 12. The Uses of Glycoprocessing Enzymes in Synthesis385
- 12.1 Introduction385
- 12.2 Glycosidases387
- 12.3 Glycosyltransferases413
- 12.4 Overall summary423
- References423
- Index427
Each chapter in this book details a particular theme associated with carbohydrate synthesis. A brief review of the subject area is provided, but the emphasis in all cases is on describing efficient practical methods to effect the transformations described.
In order for the roles of carbohydrates to be thoroughly analysed and assessed, glycobiologists require access to defined target carbohydrates in useful quantities. Thus carbohydrates and glycoconjugates are now recognized as important targets for total synthesis programmes and it is essential to develop efficient regio- and stereoselective methods for the synthesis of carbohydrates. Whilst carbohydrates can sometimes be isolated from natural sources, synthetic strategies often offer the advantage of allowing access to larger quantities of material as well as entry to analogues of the natural carbohydrates.
* The latest volume in the long standing Best Synthetic Methods series
* Clear chapter by chapter breakdown of carbohydrate synthesis themes with examples of good practical methods for common carbohydrate syntheses.