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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.
Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164
Scheme 1: Iterative synthesis of trisaccharide 66.
Scheme 2: Proposed mechanisms for TMSBr-mediated synthesis of 2-deoxyglycosides in the presence of TPPO.
Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183
Figure 1: (a) Synthesis sequence for the preparation of building blocks 4 and 5; (b) Retrosynthetic analysis ...
Scheme 1: Reagents and conditions: (i) PhI(OAc)2, BF3·Et2O, CH2Cl2, −40 °C; then Ac2O, pyridine; (ii) N2H4·Ac...
Scheme 2: Reagents and conditions. (i) TMSOTf, DCM, −10 °C, 80%; (ii) NaOMe, MeOH; then KOH, MeOH, 60 °C; the...
Scheme 3: Automated synthesis of 20. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 4: Automated synthesis of 16. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 5: Automated synthesis of 27. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 6: Automated synthesis of 30. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 7: Reagents and conditions: (i) 10% DMF in PBS buffer pH 7.5, overnight, 80%.