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: 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 View Scheme

1: 95 percent / tetrahydrofuran; diethyl ether / 72 h / 20 °C 2: 94.3 percent / NaH / tetrahydrofuran / 1 h / -15 - -10 °C 3: 96.7 percent / aq. NaOH / methanol / 72 h 4: 91.8 percent / H2 / Pd/C / ethanol; H2O / 120 h / 20 °C / 1551.44 Torr View Scheme