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Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295
Graphical Abstract
Figure 1: Representative structures of bacterial glycans containing sialic acid.
Scheme 1: Concise synthesis of 2,7-anhydrosialic acid derivatives 2–6. Conditions for the preparation of 2 an...
Figure 2: a) ORTEP diagram of compound 4. Thermal ellipsoids indicate 50% probability. b) HMBC spectrum of 6.
Scheme 2: N- and C-1-functionalization of 2.
Scheme 3: Mechanism of the SnCl4-catalyzed acetolysis of 2,7-anhydro derivatives 15. R = Me, Bn, PG = electro...
Scheme 4: Synthesis and acetolysis of 2,7-anhydro derivatives 21 and 25.
Figure 3: HMBC spectrum of carbohydrate 22.
Scheme 5: Attempted acetolysis of 2,7-anhydro-NeuN3-based disaccharides 29, 33, and 37.