Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars.
The discovery of new methods for stereoselective glycoside synthesis and convergent oligosaccharide assembly has been critical for the area of glycosciences. At the heart of this account is the discussion of the approaches for stereoselective synthesis of glycosides of 2-amino-2-deoxysugars that have emerged during the past two decades. The introductory part provides general background information and describes the key features and challenges for the synthesis of this class of compounds. Subsequently, major approaches to the synthesis of 2-amino-2-deoxyglycosides are categorized and discussed. Each subsection elaborates on the introduction (or protection) of the amino functionality, synthesis of glycosyl donors by introduction of a suitable leaving group, and glycosidation. Wherever applicable, the deprotection of a temporary amino group substituent and the conversion onto the natural acetamido functionality is described. The conclusions part evaluates the current standing in the field and provides a perspective for future developments.
Bongat
Aileen F G
AF
Department of Chemistry and Biochemistry, University of Missouri--St. Louis, One University Blvd., St. Louis, MO 63121, USA.
Demchenko
Alexei V
AV
D000577:Amides / Q000737:chemistry; D000606:Amino Sugars / Q000737:chemistry*; D000617:Aminoglycosides / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D010797:Phthalimides / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
D000577:Amides; D000606:Amino Sugars; D000617:Aminoglycosides; D001386:Azides; D002219:Carbamates; D004852:Epoxy Compounds; D010797:Phthalimides; D013451:Sulfonic Acids; D014230:Triazoles