toluene-4-sulfonic acid in N,N-dimethyl-formamide T=-10°C; 2 h;

toluene-4-sulfonic acid in tetrahydrofuran T=25°C; 14 h; Yield given;

toluene-4-sulfonic acid Ambient temperature;

copper(II) sulfate

sulfuric acid T=100°C; 4 h;

1: 1.) di-n-butyltin oxide; 2.) n-Bu4NI / 1.) MeOH, reflux, 2 h; 2.) benzene, reflux, 2 h 2: pyridine / 0.5 h / Ambient temperature 3: 95 percent / H2 / 10percent Pd(OH)2/C / methanol / 12 h 4: 92 percent / MS 4A, MeOTf / CH2Cl2 / 18 h / Ambient temperature 5: 1.) H2NNH2*H2O; 2.) DMAP / 1.) EtOH, 90 deg C, 24 h; 2.) pyridine, 12 h 6: 90 percent / NaOMe / methanol / 20 h / Ambient temperature View Scheme

T=37°C; 80 h; glycosidase precipitate (from livers of the mollusc Chamelea gallina), 0.03M sodium citrate/phosphate buffer pH 5.8; Yields of byproduct given;

1: dibutyltin oxide, tetraethylammonium bromide 2: 93 percent / toluene-p-sulfonic acid / dimethylformamide / 1.5 h / 70 °C / 12 Torr 3: 72 percent / mercury(II) cyanide, molecular sieve 3 Angstroem / acetonitrile / 24 h / Ambient temperature 4: 95 percent / KOH / dioxane 5: 92 percent / aq. 90percent acetic acid / 2 h / 85 °C 6: 92 percent / H2, 10percent Pd/C / methanol / Ambient temperature View Scheme

1: 1.) di-n-butyltin oxide; 2.) n-Bu4NI / 1.) MeOH, reflux, 2 h; 2.) benzene, reflux, 2 h 2: pyridine / 0.5 h / Ambient temperature 3: 95 percent / H2 / 10percent Pd(OH)2/C / methanol / 12 h 4: 92 percent / MS 4A, MeOTf / CH2Cl2 / 18 h / Ambient temperature 5: 1.) H2NNH2*H2O; 2.) DMAP / 1.) EtOH, 90 deg C, 24 h; 2.) pyridine, 12 h 6: 90 percent / NaOMe / methanol / 20 h / Ambient temperature View Scheme

T=37°C; 80 h; glycosidase precipitate (from livers of the mollusc Chamelea gallina), 0.03M sodium citrate/phosphate buffer pH 5.8; Yields of byproduct given;