Glycoside Synthesis from 1‐Oxygen Substituted Glycosyl Donors: Sections 3.1 and 3.2 (2008)

This chapter contains sections titled: Hemiacetals and O-Acyl/Carbonyl Derivatives Introduction Dehydrative Glycosylation via Electrophilic Activation of C1-Hemiacetals Acid Activation of C1-Hemiacetals Hemiacetal Activation with Silicon Electrophiles Hemiacetal Activation with Phosphorus Electrophiles Hemiacetal Activation with Sulfur Electrophiles Hemiacetal Activation with Carbon Electrophiles Other Methods Glycosylation with Anomeric Esters Glycosyl Acetate and Glycosyl Benzoate Donors Activation of O-Carbonyl Derivatives Conclusion Representative Experimental Procedures Representative Procedure for Preparation of C1-Hemiacetal Donors Through a Peracylation-Selective Anomeric Deacylation Sequence Representative Procedure for Brønsted Acid Promoted Glycosylation with C1-Hemiacetal Donors Using Methoxyacetic Acid Representative Procedure for Lewis Acid Promoted Glycosylation with C1-Hemiacetal Donors Using Sn(OTf)2 and LiClO4 Representative Procedure for Silicon Promoted Glycosylation with C1-Hemiacetal Donors Using Me3SiBr and CoBr2 Representative Procedure for Mitsunobu-Type Glycosylation with C1-Hemiacetal Donors and Phenol Glycosyl Acceptors Representative Procedure for Appel-Type Glycosylation with C1-Hemiacetal Donors Representative Procedure for Nosyl Chloride Promoted Glycosylation with C1-Hemiacetal Donors Representative Procedure for Diphenyl Sulfoxide and Triflic Anhydride Promoted Glycosylation with C1-Hemiacetal Donors Representative Procedure for Carbodiimide Promoted Glycosylation with C1-Hemiacetal Donors Representative Procedure for Carbonyl Promoted Glycosylation with C1-Hemiacetal Donors Using Trichloroacetic Anhydride Representative Procedure for Lewis Acid Promoted Glycosylation with Glycosyl Acetate Donors Using SnCl4 Representative Procedure for Iodotrimethylsilane and Phosphine Oxide Promoted Glycosylation with Glycosyl Acetate Donors Representative Procedure for Lewis Acid Promoted Glycosylation with TOPCAT Glycosyl Donor Using Silver Triflate Representative Procedure for TMS Triflate Promoted Glycosylation with Glycosyl N-Tosyl Carbamate Donors Representative Procedure for Trityl Salt Promoted Glycosylation with Glycosyl Phenyl Carbonate Donors References Glycoside Synthesis from 1-Oxygen-Substituted Glycosyl Imidates Introduction Methodological Aspects Preparation of Anomeric O-Trichloroacetimidates Glycosidation of O-Glycosyl Trichloroacetimidates Synthesis of Oligosaccharides β-Glucosides, β-Galactosides, α-Mannosides and Others Aminosugar-Containing Oligosaccharides 1,2-cis Glycosides Miscellaneous Oligosaccharides Synthesis of Glycoconjugates Glycosphingolipids and Mimics Glycosyl Phosphatidyl Inositol Anchors Glycosyl Amino Acids and Glycopeptides Saponins Other Natural Products and Derivatives Miscellaneous Glycoconjugates Solid-Phase Oligosaccharide Synthesis Trifluoroacetimidates Preparation and Activation Application to Target Synthesis Conclusions and Outlook Experimental Procedures Typical Procedure for the Preparation of O-Glycosyl Trichloroacetimidates Typical Procedure for the Glycosylation with O-Glycosyl Trichloroacetimidates Typical Procedure for the Preparation of O-Glycosyl N-Phenyl Trifluoroacetimidates Typical Procedure for the Glycosylation with O-Glycosyl N-Phenyl Trifluoroacetimidates References