6533b839fe1ef96bd12a6704
RESEARCH PRODUCT
A new method of anomeric protection and activation based on the conversion of glycosyl azides into glycosyl fluorides
Horst KunzWolfgang Brödersubject
AzidesMagnetic Resonance Spectroscopyanimal structuresAnomerGlycosylationOptical RotationMolecular Sequence DataCarbohydrate synthesismacromolecular substancesBiochemistryKoenigs–Knorr reactionAnalytical ChemistryFluoridesStructure-Activity Relationshipchemistry.chemical_compoundCarbohydrate ConformationOrganic chemistryGlycosylGlycosidesGlycosyl donorMolecular StructureOrganic ChemistryChemical glycosylationGlycosyl acceptorGeneral Medicinecarbohydrates (lipids)Carbohydrate Sequencechemistrylipids (amino acids peptides and proteins)description
Glycosyl azides provide reliable anomeric protection stable to conditions for hydrolytic removal of ester groups, for reductive opening or release of acetalic diol protection, for the introduction of ether-type protection, and for glycosylation processes. The utility of this anomeric protection is further enhanced as glycosyl azides may be converted into glycosyl fluorides, which can be activated for glycosylation reactions. To this end, glycosyl azides have been subjected to 1,3-dipolar cycloaddition with di-tert-butyl acetylenedicarboxylate. On treatment with hydrogen fluoride-pyridine complex the N-glycosyl triazole derivatives directly give glycosyl fluorides.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1993-10-18 | Carbohydrate Research |