3,3-dimethyldioxirane in dichloromethane; acetone 48 h; Ambient temperature;

1: methanephosphonic acid dimethyl ester With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Metallation; 0.5 h; 2: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside in tetrahydrofuran; hexane T=-78°C; Addition; 0.25 h;

1: 7.5 percent / P(NMe2)3 / CH2Cl2 2: 54 percent / 4-chloroperoxybenzoic acid; hydroquinone / CH2Cl2 / 16 h / 20 °C 3: 95 percent / NaN3 / dimethylformamide / 5 h / 20 °C 4: tetrahydrofuran / 2 h / 24 °C 5: 904 mg / tetrahydrofuran / 72 h / 20 °C 6: 100 percent / HCl; water / tetrahydrofuran / 0.67 h / 20 °C 7: 97 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.33 h / 20 °C 8: 99 percent / NH3 / methanol / 4 h / 37 °C 9: 100 percent / H2 / Pd/C / ethyl acetate / 0.5 h / 20 °C 10: 100 percent / CF3COOH; water / 2 h / 0 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) from -70 deg C to RT, 2 h 2: 95 percent / CH3ONa / methanol / 24 h / Ambient temperature 3: 80 percent / CrO3, pyridine / CH2Cl2 / 1 h / 14 - 25 °C 4: 42 percent / K2CO3, 18-crown-6 / benzene / 0.67 h / 56 °C 5: 97 percent / NaBH4, CeCl3*7H2O / methanol / 0.17 h / 0 - 5 °C 6: 100 percent / Et3N / CH2Cl2 / 0.17 h / -5 - 0 °C 7: 74 percent / LiN3, P(NMe2)3 / dimethylsulfoxide / Ambient temperature 8: H2 / Lindlar's catalyst / butan-1-ol / 3 h / 760 Torr 9: Et3N / butan-1-ol / 20 h / Heating 10: conc. HCl / 42 h / Ambient temperature 11: 70 percent / liquid NH3 / methanol / 18 h / 60 °C 12: 50 percent / 1 M BCl3 / CH2Cl2; hexane / 2.5 h / -75 °C View Scheme