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23. Selected spectral data of 5: a colourless oil; ½a D24
ꢃ
+32.0 (c 0.165, CHCl3); 1H
NMR (C6D6, 400 MHz, 7.15 ppm for C6HD5) d 0.002 (6H, s) 0.08 (9H, s), 0.24
(9H, s), 0.92 (9H, s), 1.18 (3H, s), 1.31 (1H, br d, J = 13.5 Hz), 1.44 (3H, s), 1.70–
1.82 (3H, m), 2.06–2.15 (3H, m), 2.28 (1H, br dq, J = 4.8, 12.6 Hz), 3.25–3.40
(2H, m), 3.31 (3H, s), 3.58 (1H, br ddd, J = 2.3, 11.3, 12.6 Hz), 3.66 (1H, br s),
4.02 (1H, br dd, J = 4.8, 11.3 Hz), 4.09 (1H, dd, J = 1.8, 5.6 Hz), 4.14–4.19 (1H, m),
4.22–4.29 (1H, m), 4.36 (1H, br d, J = 10.9 Hz), 4.69 (1H, d, J = 11.5 Hz), 4.86
(1H, d, J = 11.5 Hz), 5.49 (1H, s), 6.79 (2H, d, J = 8.7 Hz), 6.88–6.98 (3H, m),
7.11–7.16 (1H, m), 7.23–7.30 (4H, m), 7.75 (2H, br d, J = 7.8 Hz), 7.85–7.89 (2H,
m); 13C NMR (C6D6, 100 MHz, 128.0 ppm for C6D6) d ꢀ4.7 (CH3), ꢀ4.2 (CH3), 1.1
(CH3 ꢂ 3), 2.6 (CH3 ꢂ 3), 17.9 (C), 22.5 (CH3), 25.9 (CH3 ꢂ 3), 27.4 (CH2), 27.9
(CH3), 36.3 (CH2), 44.6 (CH2), 47.4 (CH2), 52.7 (CH2), 54.7 (CH3), 66.6 (CH2), 69.7
(CH), 72.3 (CH), 73.4 (CH2), 74.8 (C), 78.6 (CH), 83.5 (C), 85.9 (CH), 88.8 (CH),
102.0 (CH), 114.0 (CH ꢂ 2), 126.6 (CH ꢂ 2), 128.3 (CH ꢂ 4), 128.7 (CH), 129.2
(CH ꢂ 2), 130.4 (CH ꢂ 2), 130.8 (C), 133.0 (CH), 140.1 (C), 140.8 (C), 159.8 (C);
IR (film) mmax 3066, 3035, 2955, 2896, 2857, 1612, 1586, 1514, 1463, 1447,
1369, 1305, 1249, 1211, 1173, 1098, 1038, 938, 838, 776, 751, 697, 689,
650 cmꢀ1; HR-FDMS calcd for C48H76O10Si3S [M+]: 928.4467, found: 928.4467.
15. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113,
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4733; (b) Tomioka, H.; Suzuki, T.; Nozaki, H.; Oshima, K. Tetrahedron Lett. 1982,
23, 3387.