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Beilstein J. Org. Chem. 2019, 15, 137–144, doi:10.3762/bjoc.15.14
Graphical Abstract
Scheme 1: Retrosynthetic analysis for the preparation of CS oligosaccharides. Lev = levulinyl; Piv = pivaloyl...
Scheme 2: Reagents and conditions: a) TMSOTf, CH2Cl2, 0 °C, 30 min, 97%; b) (HF)n·Py, THF, 0 °C, 20 h, 90%; c...
Scheme 3: Reagents and conditions: a) C8F17CH2CH2COCl, Et3N, DMAP, DMF/CH2Cl2, 0 °C to rt, 6 h, 70%; b) Ac2O,...
Scheme 4: Reagents and conditions: a) TMSOTf, CH2Cl2, 0 °C, 30 min, 25% (14α) + 33% (14β).
Scheme 5: Reagents and conditions: a) LiOH, H2O2, THF, −5 °C to rt, 24 h, then NaOH, MeOH, 72 h, then Ac2O, Et...
Scheme 6: Reagents and conditions: a) 2-propanol, TMSOTf, CH2Cl2, 0 °C, 30 min, 73%; b) NH2NH2·H2O, Py/AcOH, ...
Scheme 7: Reagents and conditions: a) NH2NH2·H2O, Py/AcOH, CH2Cl2, 1 h, 55%; b) TMSOTf, CH2Cl2, 0 °C, 30 min,...
Scheme 8: Reagents and conditions: a) 4-Methoxyphenol, TMSOTf, CH2Cl2, 0 °C, 50 min, 92%; b) NH2NH2·H2O, Py/A...