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Chemistry - Organic Chemistry | Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry

Electrostatic and Stereoelectronic Effects in Carbohydrate Chemistry

Miljkovic, Momcilo

2014, XII, 304 p. 297 illus., 2 illus. in color.

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  • Novel discussion of Electrostatic Effects in Carbohydrate Chemistry
  • Novel discussion of Stereoelectronic Effects in Carbohydrate Chemistry
  • Extremely detailed references
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.

Content Level » Research

Keywords » Carbohydrate Chemistry - Electrostatic Interactions - Glycobiology - Glycoside - Organic Chemistry - Stereochemistry of Carbohydrate Reactions - Stereoelectronic

Related subjects » Organic Chemistry

Table of contents 

Chapter 1- Intramolecular Electrostatic Interacations

1.1 - Introduction

1.2- Intramolecular Electrostatic Interactions


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


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


Chapter 4- Conformation and Chemistry of Oxocarbenium Ion

4.1- Conformation and Chemistry of Oxocarbenium Ion


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


Chapter 6- Stereoelectronic Effects in Nucleosides and Nucleotides

6.1- Stereoelectronic effects in nucleosides and nucleotides


Chapter 7- Free Radical Cyclizations

7.1- Free-radical cyclizations


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


Author Index

Subject Index          

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