10 Pd/C; hydrogen in ethyl acetate 14 h;

L-Selectridereg; in tetrahydrofuran T=-78°C; 0.5 h;

1: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h 2: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 3: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 4: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 85 percent / N-methylmorpholine N-oxide, 4A molecular sieves, tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 2: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h 3: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 4: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 5: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 63 percent / <PhC(CF3)2O>SPh2 / tetrahydrofuran / 3 h / Ambient temperature 2: 1.) POCl3, 2.) NaBH4 3: 80 percent / NaOH, EtOH / 26 h 4: 85 percent / N-methylmorpholine N-oxide, 4A molecular sieves, tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 5: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h 6: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 7: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 8: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 1.) POCl3, 2.) NaBH4 2: 80 percent / NaOH, EtOH / 26 h 3: 85 percent / N-methylmorpholine N-oxide, 4A molecular sieves, tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 4: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h 5: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 6: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 7: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 80 percent / NaOH, EtOH / 26 h 2: 85 percent / N-methylmorpholine N-oxide, 4A molecular sieves, tetra-n-propylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 3: 1.) LDA, HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1.5 h 4: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 5: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 6: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 97 percent / H2 / 10percent Pd/C / methanol / 0.25 h / 760 Torr / Ambient temperature 2: 82 percent / K2CO3, MeOH / 8 h / Ambient temperature 3: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: pyridine / 12 h 2: TFA / tetrahydrofuran / 1 h / Heating 3: NaOMe / methanol / 12 h 4: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 5: 85 percent / NaCNBH3 / methanol / 48 h 6: 75 percent / aq. HCl / acetone / 2 h / Heating 7: 100 percent / H2 / Pd/C / methanol 8: DMSO; Ac2O / 16 h 9: NaBH4 / propan-2-ol / 20 h 10: glacial acetic acid / 48 h / Heating View Scheme

1: TFA / tetrahydrofuran / 1 h / Heating 2: NaOMe / methanol / 12 h 3: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0 4: 85 percent / NaCNBH3 / methanol / 48 h 5: 75 percent / aq. HCl / acetone / 2 h / Heating 6: 100 percent / H2 / Pd/C / methanol 7: DMSO; Ac2O / 16 h 8: NaBH4 / propan-2-ol / 20 h 9: glacial acetic acid / 48 h / Heating View Scheme