Synthetic strategies in carbohydrate chemistry /

Synthetic Strategies in Carbohydrate Chemistry covers carbohydrate synthesis and its widespread application in various disciplines including catalysis. Basic and advanced aspects of carbohydrates are covered, starting with a brief introduction and then followed by protection-deprotection strategies...

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Detalles Bibliográficos
Clasificación:Libro Electrónico
Otros Autores: Tiwari, Vinod Kumar (Editor )
Formato: Electrónico eBook
Idioma:Inglés
Publicado: Amsterdam, Netherlands : Elsevier, [2024]
Temas:
Carbohydrates > Synthesis.
Glucides > Synth�ese.
Acceso en línea:Texto completo
Tabla de Contenidos:
  • Front Cover
  • Synthetic Strategies in Carbohydrate Chemistry
  • Copyright Page
  • Contents
  • List of contributors
  • Foreword
  • Preface
  • List of abbreviations
  • 1 Glycosidic bond formation methodology: challenges and impact in oligosaccharide synthesis
  • 1.1 Introduction
  • 1.2 Complexity of carbohydrates
  • 1.3 General aspects of oligosaccharide synthesis
  • 1.3.1 Anomeric effect
  • 1.3.2 Background on classical approaches
  • 1.3.3 Mechanistic studies
  • 1.3.3.1 Armed-disarmed approach
  • 1.3.3.2 Active-latent glycosylation
  • 1.3.3.3 Remote participation
  • 1.4 Glycosylation reactions
  • 1.4.1 Glycosyl donors
  • 1.4.1.1 Glycosyl chlorides and bromides
  • 1.4.1.2 Glycosyl iodides
  • 1.4.1.3 Glycosyl fluorides
  • 1.4.1.4 Thioglycosides
  • 1.4.1.5 Glycosyl trichloroacetimidates
  • 1.4.2 Role of acceptors
  • 1.5 Conclusions and future outlook
  • References
  • 2 Recent advances in stereoselective intramolecular O-glycosylation
  • 2.1 Introduction
  • 2.2 Molecular clamping approach
  • 2.3 Intramolecular aglycon delivery concept
  • 2.4 Leaving group approach
  • 2.5 Conclusions and future outlook
  • Acknowledgments
  • References
  • 3 Thioglycoside-based glycosylations in oligosaccharide synthesis
  • 3.1 Introduction
  • 3.2 Preparation of thioglycosides
  • 3.2.1 One-pot synthesis of thioglycosides from unprotected sugars
  • 3.3 Activation of thioglycoside donors with various promoters
  • 3.4 Thioglycosides for chemoselective glycosylations
  • 3.4.1 Type A chemoselective glycosylations
  • 3.4.2 Type B chemoselective glycosylations
  • 3.4.3 Type C chemoselective glycosylations
  • 3.4.4 One-pot chemoselective glycosylations
  • 3.5 Orthogonal glycosylations
  • 3.5.1 Orthogonal glycosylations of thioglycoside acceptors with halide glycosyl donors
  • 3.5.2 Orthogonal glycosylations between trichloroacetimidate donors and thioglycoside acceptors
  • 3.5.3 Orthogonal coupling of thioglycoside acceptors with N-phenyltrifluoroacetimidate donors
  • 3.5.4 Orthogonal glycosylations of thioglycoside acceptors with other glycosyl donors
  • 3.5.5 Thioglycoside-based one-pot orthogonal glycosylations
  • 3.6 Preactivation-based glycosylation strategies
  • 3.6.1 Preactivation glycosylations based on the AgOTf/p-ArSCl promoter system
  • 3.6.2 Preactivation-based one-pot glycosylations
  • 3.7 Summary and future outlook
  • References
  • 4 General strategy for the synthesis of N-glycosides
  • 4.1 Introduction
  • 4.2 Nucleosides and their derivatives found in nature
  • 4.3 General strategy for the chemical synthesis of nucleosides and other N-glycosides
  • 4.3.1 Chemical synthesis of nucleosides via N-glycosylation
  • 4.3.1.1 Glycosyl acetates
  • 4.3.1.2 Glycosyl halide
  • 4.3.1.3 Thioglycosides
  • 4.3.1.4 Anhydroses
  • 4.3.1.5 Pentenyl glycosides
  • 4.3.1.6 Propargyl-1,2-orthoesters
  • 4.3.1.7 Glycosyl ortho-hexynylbenzoates

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