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. INDICE: 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. .
- ISBN: 978-3-527-33987-7
- Editorial: Wiley VCH
- Encuadernacion: Cartoné
- Páginas: 375
- Fecha Publicación: 25/01/2017
- Nº Volúmenes: 1
- Idioma: Inglés