Reaction Steps
A mixture of alkyne 59 (100 mg, 0.11 mmol) and 10% Pd/C (50 mg, 0.04 mmol) in MeOH (15 mL) was stirred at 20° C. under H2 (60 psi) for 2.5 h. The mixture was filtered through Celite®, washed with MeOH (100 mL), the solvent was evaporated and the residue was dried to give the carbamate 60 (85 mg, 85%) as a white gum, which was used in the next step without further purification: 1H NMR δ 9.22 (t, J=5.8 Hz, 1H, CONH), 8.57 (d, J=1.8 Hz, 1H, H-2′), 8.46 (dd, J=4.7, 1.6 Hz, 1H, H-6′), 7.99 (br d, J=8.6 Hz, 2H, H-2, H-6), 7.89 (br d, J=8.6 Hz, 2H, H-3, H-5), 7.73 (dt, J=7.9 1.9 Hz, 1H, H-4′), 7.68 (br d, J=8.3 Hz, 2H, H-2″, H-6″), 7.44 (br d, J=8.3 Hz, 2H, H-3″, H-5″), 7.36 (ddd, J=7.9, 4.8, 0.6 Hz, 1H, H-5′), 6.73 (t, J=5.5 Hz, 1H, NHCO2), 4.64 (s, 2H, CH2SO2), 4.51 (d, J=5.8 Hz, 2H, CH2NH), 3.43-3.50 (m, 20H, CH2O), 3.36 (br t, J=6.3 Hz, 4H, H-3′″, H-20′″), 3.05 (br q, J=5.9 Hz, 2H, H-21′″), 2.71 (br t, J=7.6 Hz, 2H, H-r), 2.12 (s, 3H, CH3), 1.79 (br q, J=7.1 Hz, 2H, H-2′″), 1.36 [s, 9H, (CH3)3].
