1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 2: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: NMO; OsO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 3 h / 20 °C 2.1: NaIO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 2 h / 20 °C 3.1: 8.8 g / t-BuOK / tetrahydrofuran / 6 h / 20 °C 4.1: lithium borohydride / tetrahydrofuran / 0.5 h / 20 °C 4.2: tetrahydrofuran; methanol / 24 h / 20 °C 5.1: 3.9 g / NMO; TPAP / CH2Cl2 / 18 h / 20 °C 6.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 6.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 7.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 8.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 9.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 10.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 11.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 13.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 14.1: K2CO3; MeOH / 15 h / 20 °C 15.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 16.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 17.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 18.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: 8.8 g / t-BuOK / tetrahydrofuran / 6 h / 20 °C 2.1: lithium borohydride / tetrahydrofuran / 0.5 h / 20 °C 2.2: tetrahydrofuran; methanol / 24 h / 20 °C 3.1: 3.9 g / NMO; TPAP / CH2Cl2 / 18 h / 20 °C 4.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 4.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 5.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 6.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 7.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 8.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 9.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 11.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 12.1: K2CO3; MeOH / 15 h / 20 °C 13.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 14.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 15.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 16.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: lithium borohydride / tetrahydrofuran / 0.5 h / 20 °C 1.2: tetrahydrofuran; methanol / 24 h / 20 °C 2.1: 3.9 g / NMO; TPAP / CH2Cl2 / 18 h / 20 °C 3.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 3.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 4.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 5.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 6.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 7.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 8.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 10.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 11.1: K2CO3; MeOH / 15 h / 20 °C 12.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 13.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 14.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 15.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: 3.9 g / NMO; TPAP / CH2Cl2 / 18 h / 20 °C 2.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 2.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 3.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 4.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 6.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 7.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 9.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 10.1: K2CO3; MeOH / 15 h / 20 °C 11.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 12.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 13.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 14.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 1.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 2.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 3.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 4.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 5.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 6.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 8.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 9.1: K2CO3; MeOH / 15 h / 20 °C 10.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 11.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 12.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 13.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 2: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 3: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 4: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 5: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 6: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 7: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 8: K2CO3; MeOH / 15 h / 20 °C 9: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 10: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 11: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 12: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 2: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 3: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 4: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 5: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 6: K2CO3; MeOH / 15 h / 20 °C 7: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 8: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 9: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 10: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 2: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 4: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 5: K2CO3; MeOH / 15 h / 20 °C 6: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 7: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 8: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 9: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 2: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 3: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 4: K2CO3; MeOH / 15 h / 20 °C 5: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 6: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 7: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 8: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme