hydrogen; palladium on activated charcoal in ethanol Hydrogenolysis; 5 h;

trifluoroacetic acid T=20°C; 0.133333 h;

1: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 2: pyridine / 48 h / 5 °C 3: 59.4 mg / TMSCl / pyridine 4: 25.8 mg / pyridine; H2O / 19 h / 20 °C 5: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 6: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 100 percent / pyridine / 12 h / 20 °C 2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C 3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C 4: NaH / tetrahydrofuran / 12 h / -20 °C 5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 6: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 7: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 8: pyridine / 48 h / 5 °C 9: 59.4 mg / TMSCl / pyridine 10: 25.8 mg / pyridine; H2O / 19 h / 20 °C 11: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 12: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 2: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 3: pyridine / 48 h / 5 °C 4: 59.4 mg / TMSCl / pyridine 5: 25.8 mg / pyridine; H2O / 19 h / 20 °C 6: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 7: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C 2: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C 3: NaH / tetrahydrofuran / 12 h / -20 °C 4: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 5: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 6: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 7: pyridine / 48 h / 5 °C 8: 59.4 mg / TMSCl / pyridine 9: 25.8 mg / pyridine; H2O / 19 h / 20 °C 10: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 11: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C 2: NaH / tetrahydrofuran / 12 h / -20 °C 3: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 4: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 5: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 6: pyridine / 48 h / 5 °C 7: 59.4 mg / TMSCl / pyridine 8: 25.8 mg / pyridine; H2O / 19 h / 20 °C 9: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 10: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 2: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 3: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 4: pyridine / 48 h / 5 °C 5: 59.4 mg / TMSCl / pyridine 6: 25.8 mg / pyridine; H2O / 19 h / 20 °C 7: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 8: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: NaH / tetrahydrofuran / 12 h / -20 °C 2: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 3: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 4: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 5: pyridine / 48 h / 5 °C 6: 59.4 mg / TMSCl / pyridine 7: 25.8 mg / pyridine; H2O / 19 h / 20 °C 8: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 9: 36 percent / TFA / 0.13 h / 20 °C View Scheme

1: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 2: 36 percent / TFA / 0.13 h / 20 °C View Scheme