Selective Glycosylations

Synthetic Methods and Catalysts

Bennett, Clay S. (Herausgeber)

1. Auflage März 2017
XVI, Seiten, Hardcover
391 Abbildungen
29 Tabellen
Monographie

ISBN: 978-3-527-33987-7

Wiley-VCH, Weinheim

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Kurzbeschreibung

By providing the latest advances and mechanistic aspects, this is an invaluable reference for researchers interested in developing novel stereoselective approaches to chemical glycosylation.

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A comprehensive summary of novel approaches to the stereoselective construction of glycosidic linkages, covering modern glycosylation methods and their use and application in natural product synthesis and drug discovery.
Clearly divided into five sections, the first describes recent advances in classical methodologies in carbohydrate chemistry, while the second goes on to deal with newer chemistries developed to control selectivity in glycosylation reactions. Section three is devoted to selective glycosylation reactions that rely on the use of catalytic promoters. Section four describes modern approaches for controlling regioselectivity in carbohydrate synthesis. The final section focuses on new developments in the construction of "unusual" sugars and is rounded off by a presentation of modern procedures for the construction of glycosylated natural products.
By providing the latest advances in glycosylation as well as information on mechanistic aspects of the reaction, this is an invaluable reference for both specialists and beginners in this booming interdisciplinary field that includes carbohydrate chemistry, organic synthesis, catalysis, and biochemistry.

PART I. INTRODUCTION
1) Stereoselective Glycosylations - Additions to Oxocarbenium Ions
2) Application of Armed, Disarmed, Superarmed, and Superdisarmed Building Blocks in Stereocontrolled Glycosylation and Expeditious Oligosaccharide Synthesis
3) Solvent Effect on Glycosylation

PART II. STEREOCONTROLLED APPROACHES TO GLYCAN SYNTHESIS
4) Intramolecular Aglycon Delivery toward 1,2-cis Selective Glycosylation
5) Chiral Auxiliaries in Stereoselective Glycosylation Reactions
6) Glycosylation with Glycosyl Sulfonates

PART III. CATALYTIC ACTIVATION OF GLYCOSIDES
7) Stereoselective C-Glycosylation from Glycal Scaffolds
8) Brønsted- and Lewis-Acid-Catalyzed Glycosylation
9) Nickel-Catalyzed Stereoselective Formation of 1,2-cis-2-Aminoglycosides
10) Photochemical Glycosylation

PART IV. REGIOSELECTIVE FUNCTIONALIZATION OF MONOSACCHARIDES
11) Regioselective Glycosylation Methods
12) Regioselective, One-Pot Functionalization of Carbohydrates

PART V. STEREOSELECTIVE SYNTHESIS OF DEOXY SUGARS, FURANOSIDES, AND GLYCOCONJUGATE SUGARS
13) Selective Glycosylations with Deoxy Sugars
14) Selective Glycosylations with Furanosides
15) De novo Asymmetric Synthesis of Carbohydrate Natural Products
16) Chemical Synthesis of Sialosides

Clay S. Bennett is an associate professor in the Department of Chemistry at Tufts University, Medford, USA. He received his B.A. in chemistry from Connecticut College (New London, USA) in 1999, where he carried out undergraduate research in bioorganic chemistry with Prof. Bruce Branchini. He then entered the University of Pennsylvania, USA, where he studied natural products total synthesis with Prof. Amos B. Smith, III. Upon obtaining his Ph.D. in 2005 he joined the lab of Prof. Chi-Huey Wong at the Scripps Research Institute, San Diego, California, USA, to study carbohydrate chemistry as a postdoctoral researcher. His current research interests focus on developing new stereoselective glycosylation reactions and application of these technologies to the synthesis carbohydrate-based vaccines and oligosaccharide antibiotics.

C. S. Bennett, Tufts University, Medford, USA