pyridine T=50 - 60°C; 1 h;

trimethylsilyl trifluoromethanesulfonate in dichloromethane T=20°C; 0.166667 h; Inert atmosphere;

tetrabutyl ammonium fluoride in tetrahydrofuran Ambient temperature;

in N,N-dimethyl-formamide T=100°C; 0.0833333 h;

in acetonitrile T=78 - 80°C; 3 h;

1: HCl / methanol / 12 h / Ambient temperature 2: pyridine, hexamethyldisilazane / Ambient temperature View Scheme

diethylesilane; tris(pentafluorophenyl)-borane in dichloromethane-d2 18 h; Inert atmosphereGlovebox; Reagent/catalystTime;

1: per-O-silylated α-methyl-D-glucopyranoside; benzaldehyde With trimethylsilyl trifluoromethanesulfonate in dichloromethane T=-86°C; 2 h; Molecular sieve; 2: With triethylsilane; 4-methoxy-benzaldehyde; trimethylsilyl trifluoromethanesulfonate in dichloromethane T=-86°C; 5 h; 3: acetic anhydride; benzoyl chloride With tetrabutyl ammonium fluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone Product distribution / selectivity; more than 3 stages;

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve 2: tetrabutyl ammonium fluoride / dichloromethane / 0 - 20 °C / Inert atmosphere 3: triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere View Scheme

diethylesilane; tris(pentafluorophenyl)-borane in dichloromethane-d2 18 h; Inert atmosphereGlovebox; Reagent/catalystTime;