sodium hydride in N,N-dimethyl-formamide T=0°C; Etherification; 0.5 h;

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;

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C View Scheme

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