Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry, 2014

The book deals with polar effects in carbohydrates and how these effects control the stereochemistry of carbohydrate reactions. This is important for understanding the mechanisms of certain carbohydrate reactions, including enzymatic reactions such as glycosidases, a very important group of enzymes in living matter. It is also very useful for synthetic carbohydrate chemists who would like to synthesize stereoselectively certain classes of carbohydrates. This book will be a very important source of information for practicing synthetic carbohydrate chemists. The book will also be helpful for organic chemists, or for those studying glycobiology.

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          

Novel discussion of Electrostatic Effects in Carbohydrate Chemistry

Novel discussion of Stereoelectronic Effects in Carbohydrate Chemistry

Extremely detailed references