Selective Glycosylations: Synthetic Methods and Catalysts

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) Additions to Oxocarbenium Cations
2) Armed, Super–Armed, Disarmed, and Super–Disarmed Donors in Chemical Glycosylation
3) Solvent Effects in Stereoselective Glycosylations

PART II. STEREOCONTROLLED APPROACHES TO GLYCAN SYNTHESIS
4) Intramolecular Aglycone Delivery in the Synthesis of cis–1,2–Glycosides
5) Chiral Auxiliaries in cis–1,2–Glycoside Synthesis
6) Glycosyl Iodides for Stereoselective Oligosaccharide
7) Glycosyl Sulfonates as Intermediates in SN2–like Glycosylation Reactions
8) Umpolung in Chemical Glycosylation

PART III. CATALYTIC ACTIVATION OF GLYCOSIDES
9) De Novo Oligosaccharide Synthesis
10) Bronsted Acid–Catalyzed Glycosylation
11) Transition Metal–Catalyzed Glycosylation

PART IV: REGIOSELECTIVE FUNCTIONALIZATION OF MONOSACCHARIDES
12) One–Pot Monosaccharide Protection
13) Catalytic Approaches to Regioselective Carbohydrate Functionalization

PART V. STEREOSELECTIVE SYNTHESIS OF UNUSUAL SUGARS
14) Selective Glycosylations with Deoxy–Sugar Donors
15) Selective Glycosylations with Furanoside Donors
16) Selective Glycosylations with Sialic Acid Derivatives
17) Synthesis of Natural Product Glycoconjugates

APPENDIX



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.