Page 231 - Demo

SECTION I: MOLECULAR GENETIC ENGINEERING AND BIOCHEMICAL TECHNOLOGY 235Compound 4: (6S,9R)-roseosideColorless amorphous solid1H-NMR (500 MHz, MeOD) d (ppm): 1.05 (3H, s, 12-CH3); 1.06 (3H, s, 11-CH3); 1.31 (3H, d, 6.0, 10-CH3); 1.94 (3H, brs, 13-CH3); 2.18 (1H, d, 17.0, 2-CH2); 2.55 (1H, d, 17.0, 2-CH2); 3.20 (1H, m, 2%u2019-CH); 3.24 (1H, m, 5%u2019-CH); 3.29 (1H, m, 4%u2019-CH); 3.35 (1H, m, 3%u2019-CH); 3.65 (1H, m, 6%u2019-CH2); 3.87 (1H, d, 2.0, 15.0, 6%u2019-CH2); 4.36 (1H, d, 7.5, 1%u2019-CH); 4.44 (1H, m, 9-CH); 5.87 (1H, m, 8-CH); 5.88 (1H, brs, 4-CH); 5.89 (1H, m, 7-CH).13C-NMR (125 MHz, MeOD) d (ppm): 201.36 (C-3); 167.34 (C5); 135.26 (C-7); 131.55 (C-8); 127.18 (C-4); 102.72 (C-1%u2019); 80.01 (C6); 78.08 (C-3%u2019); 78.00 (C-5%u2019); 77.33 (C-9); 75.24 (C-2%u2019); 71.63 (C-4%u2019); 62.79 (C-6%u2019); 50.69 (C-2); 42.43 (C-1); 24.67 (C-12); 23.42 (C-11); 21.19 (C-10); 19.57 (C-13).Compound 5: (7S,8R,8%u2019R)-5%u2019-methoxy isolariciresinolColorless amorphous solid1H-NMR (500 MHz, MeOD) d (ppm): 6.72 (1H, d, J = 1.5, H-2); 6.67 (1H, d, J = 8.0, H-5); 6.59 (1H, s, H-2%u2019); 6.50 (1H, dd, J = 8.0; 2.0, H-6); 4.30 (1H, d, J = 6.0, H-7); 3.87 (3H, s, 3%u2019-OMe); 3.78 (3H, s, 3-OMe); 3.60 (1H, m, Ha-9%u2019); 3.53 (1H, m, Ha-9); 3.51 (1H, m, Hb-9); 3.50 (1H, m, Hb-9%u2019); 3.37 (3H, s, 5%u2019-OMe); 2.71 (1H, dd, J= 15.0; 4.5, Ha-7%u2019); 2.57 (1H, dd, J = 15.0; 11.5, Hb-7%u2019); 1.96 (1H, m, H-8); 1.65 (1H, m, H-8%u2019).13C-NMR (125 MHz, MeOD) d (ppm): 148.66 (C-3); 148.59 (C-3%u2019); 147.62 (C-5%u2019); 145.34 (C-4); 140.11 (C-1); 138.87 (C-4%u2019); 130.13 (C-1%u2019); 126.46 (C-6%u2019); 121.74 (C-6); 115.76 (C-5); 113.43 (C2); 107.83 (C-2%u2019); 66.82 (C-9%u2019); 64.13 (C-9); 60.10 (5%u2019-OMe); 56.64 (3%u2019-OMe); 56.42 (3-OMe); 49.51 (C-8); 42.04 (C-7); 40.93 (C-8%u2019); 33.64 (C-7%u2019).