4H). 13C NMR (CDCl3, 50 MHz) 14.0, 22.six, 27.1, 29.3, 29.five, 29.7, 31.9, 39.2, 54.2, 59.7, 65.9, 68.2, 71.8, 171.six. 31P NMR (CDCl3, 160 MHz, pyrophosphate ref. ext.) -1.01. Rf (CHCl3/MeOH/H2O 65:25:4) 0.25. Anal. Calcd for C20H43N2O6P?.5H2O: C, 51.60; H, 9.96; N, 6.02; Located: C, 51.49; H, 9.99; N, 6.06. MS MH+ C20H43N2O6PH Calcd: 439.2937, Discovered: 439.2927. []D20 -5.4?(c 1.12, CHCl3/ MeOH four:1). 4.4.two. 2-Hydroxy-3-[(12-(7-mercapto-4-methylcoumarin)dodecyloxy]-3oxopropyl phosphocholine (24)–To a remedy of 23 (0.1202 g, 0.17 mmol) in two mL of CHCl3 were added 50 L of 12 M aq. HCl. The reaction mixture was stirred at area temperature for two h. At the end of your reaction to this solution was added 100 mL benzene, and the mixture was freeze-dried to give a white residue. This residue was dissolved in CHCl3/MeOH/H2O (65:25:4) and purified on a silica gel column packed with CHCl3/MeOH (4:1) and eluted with CHCl3/MeOH/H2O (65:25:4). The fractions containing the item have been isolated, evaporated, dispersed in benzene and freeze-dried to provide 24 (62 mg, 57 ) as white solid. IR (CHCl3): 3330, 1737 br, 1615, 1205 cm-1; 1H NMR (CDCl3+CD3OD, 200 MHz) 1.28 (br s, 16H), 1.69 (m, 6H), two.64 (s, 3H), two.98 (t, 2H, J = 7.2 Hz), three.24 (br s, 9H), three.36 (s, 1H), three.66 (br s, 2H), 3.68 (m, 2H), four.35 (m, 1H), six.23 (s, 1H), 7.18?.56 (m, 3H). 13C NMR (CDCl3, 50 MHz) 18.4, 25.six, 28.five, 28.7, 29.0, 29.three, 29.five, 30.5, 32.0, 54.two, 59.two, 66.three, 113.three, 113.six, 116.1, 122.9, 124.five, 143.9, 152.eight, 153.six, 161.two. 31P NMR (CDCl3, 160 MHz, pyrophosphate external reference) -1.16. Rf (CHCl3/MeOH/H2O 65:25:four) 0.31. Anal. Cald for C30H48NO9PS?/2H2O: C, 53.40; H, 7.92; N, 2.08 Found: C, 53.32; H, 7.56; N, 1.71. []D20 -3.7?(c 0.94, CHCl3/MeOH four:1). four.five. Basic process for acylation on the 2-hydroxy group of your lysophospholipid analogues 4. five.1. (20) Route II–To a remedy of (22) (0.2497 g, 0.57 mmol) in 15 mL of CHCl3 have been added 10-(7-mercapto-4-methyl-7-yl)decanoic acid (0.4129 g, 1.14 mmol), DCC (0.2352 g, 1.14 mmol), DMAP (0.1393 g, 1.14 mmol) and 0.5 g of glass beads.21 The mixture was sonicated for five h at 25 . The glass beads and the DCC-urea have been filtered off, and the filtrate was evaporated. The residue was dissolved in CHCl3/MeOH (4:1) and purified on silica gel column packed with CHCl3, and eluted initial with CHCl3/MeOH (4:1), to get rid of the impurities, and after that with CHCl3/MeOH/H2O (65:25:4) to elute the solution. The fractions containing the product have been combined, evaporated, dispersed in benzene, andTetrahedron. Author manuscript; accessible in PMC 2015 May 13.Rosseto and HajduPagefreeze-dried to give 20 (0.4-Ethynyl-1,2-dimethylbenzene custom synthesis 2767 g, 0.2454490-66-3 site 35 mmol, 62 ) as white solid (analytical information are described above, in the synthesis of the compound 20 in Route I.PMID:28630660 NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript4.five.two. 2-(12-[9H-fluoren-9-yl)methoxycarbony]amino]dodecanoyl)oxy)-3-((12((7-merapto4-methylcoumarin-7-yl)dodecyl)oxy)-3-oxopropyl phosphocholine (25)–To a option of 24 (0.4995 g, 0.8 mmol) in 25 mL CHCl3 were added 12-(9fluorenylmethoxycarbonyl)-N- aminododecanoic acid (0.9987 g, two.three mmol), DCC (0.6621 g, three.two mmol), DMAP (0.4012 g, three.two mmol) and 1 g of glass beads,21 and also the mixture was sonicated for 5 h at 25 . The glass beads and the DCC-urea had been filtered off, the filtrate was evaporated, along with the residue obtained was dissolved in CHCl3/MeOH (4:1) and purified on silica gel column packed with CHCl3 and eluted very first with CHCl3/MeOH (4:1) to take away the impurities, and t.