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Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128
Graphical Abstract
Scheme 1: The concept of using allylic reactivity enhancement to facilitate diglycoside synthesis.
Scheme 2: (i) Phosphomolybdic acid, EtOH, MeCN, 0 °C→RT, 63%; (ii) a) NaOMe, MeOH, 87%; b) TBDMSCl, imidazole...
Scheme 3: (i) DIAD, PPh3, THF, 0 °C→RT; 10, 91%; 11, 88%; 12, 76%; 13, 91%; 14, 91%; 15, 71%.
Scheme 4: (i) K2OsO4, NMO, acetone, H2O; 16, 88%; 17, 73%; (ii) Ac2O, py, 83%; (iii) MeOH, HCl (1 M aq.); 19,...
Scheme 5: (i) Cl3CCN, DBU, CH2Cl2, 99%; (ii) TMPP, Pd(dba)2, 5, Et3N, MeCN, 24, 44%; 25, 15%; 26, 5%; 27, 6%.
Figure 1: Previously synthesised amine-linked diglycosides.