Reaction Steps
The azide 73 (200 mg, 211 μmol), 3-(prop-2-ynyloxy)cholestanol (3 equiv., 267 mg), CHCl3 (2 mL), t-BuOH (2 mL), CuSO4 (50 μL of a 0.3 M aqueous solution) and sodium ascorbate (62.5 μL of a 1M aqueous solution) was stirred vigorously overnight at r.t. The solvent was evaporated and the residue purified by column chromatography (SiO2: Hexane to 2:3 Hexane:EtOAc) to yield the triazole 74 (197 mg, 68%). 1H NMR (300 MHz, CDCl3) δ 7.66 (s, 1H, triazol-H), 5.85 (d, 1H, J1,2=9.3, H-1I), 5.46-5.27 (m, 6H, H-1II, H-1II, H-2I, H-4III, H-3II, H-3III), 5.03 (dd, 1H, J3,2=9.8, J3,4=9.8, H-3I), 4.82 (dd, 1H, J2,1=4.1, J2,3=10.3, H-2), 4.72 (dd, 1H, H-2), 4.63 (s, 2H, CH2O), 4.47-4.41 (m, 2H), 4.32-3.88 (m, 9H), 3.31 (m, 1H, CHO), 2.12 (s, 6H, OAc), 2.06 (s, 3H, OAc), 2.03 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.99 (s, 3H, OAc), 1.98 (s, 3H, OAc), 1.96 (s, 3H, OAc), 1.96-0.83 (m, 31H), 1.82 (s, 3H, OAc), 0.85 (d, 3H, J=6.7, CH3), 0.82 (m, 6H, CH3), 0.76 (s, 3H, CH3), 0.60 (s, 3H, CH3).
