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Beilstein J. Org. Chem. 2019, 15, 210–217, doi:10.3762/bjoc.15.20
Graphical Abstract
Figure 1: Macrocyclic derivatives with sucrose scaffold.
Figure 2: Strategy to sucrose cryptands with additional macrocyclic unit.
Scheme 1: a) 50% NaOH, Bu4NHSO4, 74%; b) NaI, acetone, 95%; c) Na2CO3, ACN, 80 °C, 24 h, 33%.
Figure 3: A concept for synthesis of a cryptand from penta-O-benzylsucrose (2).
Scheme 2: a) MsCl, Et3N, DMAP, DCM, −78 °C to rt.; b) Na2CO3, KI, ACN, reflux.
Scheme 3: a) AllBr, TBAB, PhMe, 50% NaOH, 50 °C, 18 h, 94%; b) i. O3, DCM, −78 °C; ii. NaBH4, DCM, MeOH, rt, ...
Scheme 4: a) 50% NaOH, Bu4NHSO4, 58%; b) NaI, acetone, 95%; c) Na2CO3, ACN, 80 °C, 24 h, 45.5%.
Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227
Scheme 1: Synthesis of diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside (4).
Figure 1: Derivatives of diosgenyl glycosides 5–13.