Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry

Chapter 1- Intramolecular Electrostatic Interacations

1.1 - Introduction

1.2- Intramolecular Electrostatic Interactions

References

Chapter 2- Anomeric Effects

2.1-Anomeric effect and related stereoelectronic effects

2.2-Exo-anomeric effect

2.3-Generalized anomeric effect

2.4-Anomeric effect in systems O-C-N

2.5-Gauche effect

References

Chapter 3- Acid Catalyzed Hydrolysis of Glycosides

3.1- Oxocarbenium ion

3.2- The acid-catalyzed hydrolysis of glycosides

3.3- The acid-catalyzed hydrolysis of glycopyranosides

3.4- The acid-catalyzed hydrolysis of glycofuranosides

3.5- Some recent developments regarding the mechanism of glycoside hydrolysis

3.6- Acetolysis of glycosides

References

Chapter 4- Conformation and Chemistry of Oxocarbenium Ion

4.1- Conformation and Chemistry of Oxocarbenium Ion

References

Chapter 5- Glycosylation

5.1- Armed-disarmed concept in the synthesis of glycosidic bond

5.2- Stereoelectronic effects of substituents. Polyhydroxylated piperidines and sugars

5.3- Glycosylation reactions with conformationally armed donors

5.4- Superarmed glycosyl donors in glycosylation reactions

5.5-Regio- and stereoselectivity of glycosylation

5.6- Proton-catalyzed addition of alcohols to glycals: glycals as glycosyl donors

References

Chapter 6- Stereoelectronic Effects in Nucleosides and Nucleotides

6.1- Stereoelectronic effects in nucleosides and nucleotides

References

Chapter 7- Free Radical Cyclizations

7.1- Free-radical cyclizations

References

Chapter 8- Sulfones, Olefins, Nitrones, Glycosidic Bond, and Norrish-Young Photocyclization

8.1- Carbohydrate sulfones

8.2- Michael addition to vinyl sulfones

8.3- Glycosyl sulfones

8.4- Strecker reaction

8.5- Mercuration of carbohydrate olefins

8.6- 1,3-Dipolar cycloaddition of chiral N-(alkoxyalkyl)nitrones

8.7- Synthesis of glycosides by reduction of sugar orthoesters

8.8- Reductive cleavage of glycosidic bond

8.9- Carbohydrate degradation by oxygen

8.10 Norrish-Young photocyclization

References

Author Index

Subject Index