1: 38 percent / acetic anhydride / 1 h / Heating 2: 73 percent / sat. NH3 / methanol / 0 °C 3: 0.1 M HCl / H2O / 25 °C / pH 2.01 View Scheme

1: 39 percent / AcONa / aq. acetic acid / 24 h / Ambient temperature 2: 1.) NaH, 2.) NH3 / 1.) Me2NCHO, 18 deg C, 1 h; 2.) MeOH, 0 deg C, 19 h 3: H(1+) or OH(1-) View Scheme

1: 39 percent / AcONa / aq. acetic acid / 24 h / Ambient temperature 2: 1.) NaH, 2.) NH3 / 1.) Me2NCHO, 18 deg C, 1 h; 2.) MeOH, 0 deg C, 19 h 3: H(1+) or OH(1-) 4: 41 percent / N,N-diethylaniline / H2O; dimethylformamide / 4 h / 90 °C View Scheme

1: 36 percent / AcONa / acetic acid / 5 h / 30 °C 2: 69 percent / 1N NaOH / H2O / 3 h / Ambient temperature 3: 0.1N HCl / H2O / 25 °C / hydrolytic cleavage of the glycosidic bond in several HCl solutions View Scheme