Supplementary Materialsmolecules-25-01265-s001. 3-Hax protons providing rise to a large coupling 3diastereomer would adopt Prostaglandin E1 manufacturer a twist motorboat conformation with set up of the 2-H and 3-Hs, which would create small ideals for both 3in ppm and 3(= 9.6 Hz and 5.2 Hz, 3-H, 2 H), 4.39 (m, = 9.6 Hz and 5.2 Hz, 2-H, 2 H), 7.03 (d, = 8.0 Hz, 9-H, 1 H), 7.10 (m, 7-H, 1 H), 7.4 (m, 8-H, 1 H), 7.9 (dd, = 8.0 Hz and 1.6 Hz, 6-H, 1 H), 8.2 (br s, 4-H, 1 H). 13C NMR (100 MHz, CDCl3): = 41.3 (C-3), 73.2 (C-2), 121.3 (C-9), 122.8 (C-7), 123.9 (C-5a), 131.6 (C-6), 133.3 (C-8), 155.3 (C-9a), 170.9 (C-5). IR (KBr): 1661, 3060, 3183, 3287 cm?1. HRMS-ESI (((= 4.8 Hz, 3-H, 2 H), 4.35 (m, = 4.8 Hz, 2-H, 1 H), 4.73 (s, 5-H, 2 H), 6.97 (d, = 7.6 Hz, 9-H, 1 H), 7.01 (d, = 9.2 Hz, 6-H, 1 H), 7.09 (m, 7-H, 1 H), 7.23C7.27 (m, 6-H and 8-H, 2 H), 8.13 (dd, = 9.2 Hz and 2.8 Hz, 5-H, 1 H), 8.61 (d, = 2.8 Hz, 3-H, 1 H), 9.99 (s, 1H, -CHO). 13C-NMR (100 MHz, CDCl3): = 55.9 (C-3), 58.21 (C-5), 70.34 (C-2), 117.3 (C-9), 120.4 (C-6), 123.4 (C-7), 124.0 (C-6a), 126.7 (C-2), 129.0 (C-3), 129.3* (C-8), 129.4* (C-6), 129.8* (C-5), 139.7 (C-4), 156.7 (C-9a), 158.7 (C-1), 188.4 (-CHO). *exchangable signals. IR (KBr): 761, 1330, 1491, 1600, 1684 cm?1. HRMS-ESI Prostaglandin E1 manufacturer ((= 8.0 Hz, 6-H, 1 H), 7.15C7.20 (m, 3-H,7-H, 9-H, 3 H), 7.26-7.33 (m, 8-H, 1 H), 7.73 (s, 7-H, 1 H), 8.2 (dd, = 9.2 Hz and 2.4 Hz, 4-H, 1 H), 8.84 (d, = 2.4 Hz, 6-H, 1 H). 13C NMR (100 MHz, CDCl3): = 56.8 (C-3), 59.1 (C-5), 70.6 (C-2), 84.1 (C-2),111.8 (CN), 112.9 (CN), 118.8 (C-9), 120.8 (C-3), 121.5 (C-1), 124.1 (C-7),125.9 (C-6), 127.6 (C-5a), 128.9 (C-4), 129.4 (C-6), 129.8 (C-8), 140.9 (C-5), 156.9 (C-7), 158.2 (C-9a), 159.2 (C-2). IR (KBr): 781, 1509, 1570, 2232, 2925 cm?1. HRMS-ESI ((= 17.2 Hz, 9-Ha, 1 H), 3.48 (m, 3-Ha, 1 H), 3.71C3.76 (overlapping m, 9-Hb and 3-Hb, 2 H), 3.99C4.05 (m, 2-Ha, 1 H), 4.22 (m, = 3.6 Hz and 16.4 Hz, 2-Hb, 1 H), 4.82 (s, 15-Ha, 1 H), 6.98C7.02 (m, 16-H, 19-H, 2 H), 7.10 (d, = 9.2 Hz, 5-H, 1 H), 7.17 (m, 17-H, 1 H), Rabbit polyclonal to CREB1 7.39 (m, 18-H, 1 H), 7.97 (dd, = 9.2 Hz and 2.8 Hz, 6-H, 1 H), 8.02 (bs, 8-H, 1 H). 13C NMR (100 MHz, DMSO-((= 14.4 and 3.6 Hz, 1 H, 3-Ha), 3.24 (dd, = 14.4 and 10.8 Hz, 1 H, 3-Hb), 6.19 (dd, = 10.8 Hz and 3.6 Hz, 1 H, 2-H), 7.07-7.52 (m, 2 H, 6-H, 7-H), 7.53C7.57 (m, 4 H, 3-H, 4-H, 5-H, 8-H), 7.75 (d, 1 H, 8-H), 7.89 (m, 2 H, 2-H, 6-H), 8.00 (m, 2 H, 5-H, 7-H). 13C-NMR (90 MHz, CDCl3): = 43.9 (C-3), 76.8 (C-2), 118.2 (C-8), 121.1 (C-4a), 121.7 (C-6), 122.8 (C-8), 123.8 (C-3), 125.3 (C-6), 125.9 (C-2), 126.6 (C-7), 127.1 (C-5), 129.1 (C-4), 129.3 (C-5), 130.1 (C-8a), 133.8 (C-4a), 134.1 (C-1), 136.2 (C-7), 161.7 (C-8a), 192.2 (C-4). IR (KBr): Prostaglandin E1 manufacturer 1222, 1302, 1606, 1684, 3050 cm?1. (= 16.5 Hz and 2.5 Hz, 1 H, 3-Ha) 3.09 (dd, = 16.5 Hz and 13.0 Hz, 1 H, 3-Hb). 5.56 (dd, = 7.6 Hz, 1 H, 8-H). 13C-NMR (90 MHz, CDCl3): = 44.5 (C-3), 79.6 (C-2), 118.1 (C-8), 120.9 (C-4a), 121.6 (C-6), 123.6 (C-3), 125.3 (C-4), 126.4 (C-6, C-7), 127.0 (C-1), 127.7 (C-5), 128.1 (C-5), 128.7 (C-8), 133.1 (C-8a), 133.3 (C-4a), 135.9 (C-2), 136.2 (C-7), 161.4 (C-8a), 191.8 (C-4). IR (KBr): 1063, 1223, 1688, 3025 cm?1. (= 8.0 Hz 1 H, 9-H), 7.21 (m, 1 H, 7-H), 7.46-7.49 (m, 4 H, 2-H, 3-H, 6-H, 8-H),.