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Beilstein J. Org. Chem. 2024, 20, 1421–1427, doi:10.3762/bjoc.20.124
Graphical Abstract
Scheme 1: Preparation of cyclic oligoglucosamines a) via intramolecular glycosylation and b) via polyglycosyl...
Scheme 2: Proposed reaction mechanism of the formation of 1,6-anhydrosugar 7.
Scheme 3: Electrochemical polyglycosylation of monomer 14 with a 2,3-oxazolidinone protecting group.
Scheme 4: Proposed reaction mechanism of the formation of cyclic trisaccharide 19a.
Scheme 5: Influence of the functional group in position C-2 on the formation of the cyclic product.
Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117
Figure 1: Structures of chitin and chitosan oligosaccharides.
Figure 2: Effect of the anomeric leaving group on the yield of oligosaccharides.
Figure 3: Influence of the glycosylation temperature (T2) on the yield of oligosaccharides.
Figure 4: Influence of temperatures of anodic oxidation (T1) and glycosylation (T2).
Figure 5: MALDI–TOF MS spectra of oligosaccharides.
Figure 6: Proposed structures of byproducts of electrochemical polyglycosylation.
Figure 7: Proposed mechanisms of electrochemical polyglycosylation.
Figure 8: Oxidative potential of monosaccharide 1a, disaccharide 2a, and trisaccharide 3a.
Scheme 1: Electrochemical dimerization of tetrasaccharide 4a.
Figure 9: Influence of cycle number on the yield of longer oligosaccharides 5a (n = 5)–8a (n = 8). Conditions...