Reaction Steps
The procedure for 35 was used with alcohol 66 (1.70 g, 1.85 μmol), TBSOTf (0.94 mL, 4.07 mmol) and 2,6-lutidine (0.51 mL, 4.44 mmol) to yield 67 (1.82 g, 96%) by flash column chromatography (EtOAc/hexane 1:19) as a colorless oil: IR (CHCl3) 2956, 2856, 1471, 1448, 1254, 1092, 1004, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.77-7.75 (m, 6H), 7.57-7.47 (m, 9H), 6.02-5.87 (m, 2H), 5.76 (t, J=10.8 Hz, 1H), 5.61 (dd, J=10.8, 8.5 Hz, 1H), 4.88 (m, 1H), 4.24 (m, 1H), 3.88 (m, 4H), 3.75 (m, 1H), 2.94 (m, 1H), 2.73 (m, 1H), 1.83 (m, 2H), 1.75 (m, 2H), 1.57 (m, 1H), 1.46-1.41 (m, 2H), 1.31 (d, J=6.8 Hz, 3H), 1.30(d, J=6.3 Hz, 3H), 1.24-1.13 (m, 39H), 0.44-0.34 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 144.4, 134.4, 132.9, 132.2, 128.7, 127.7, 126.8, 86.8, 80.2, 72.3, 66.6, 65.1, 63.6, 42.4, 41.6, 38.4, 35.7, 31.6, 29.9, 26.3, 26.0, 19.6, 18.5, 18.4, 18.2, 15.1, 13.2, −2.9, −3.6, −3.7, −4.2, −5.2; LRMS (ESI) 1051.6 [M+Na]+, 918.6, 769.5, 637.4, 413.2; HRMS (ESI) calcd for C61H104O5Si4Na 1051.6859 [M+Na]+, found 1051.6848 [α]20D−8.3 (c 2.4, CHCl3).
