Hen with CHCl3/MeOH/H2O (65:25:four) to elute the solution. The fractions containing the solution had been combined, evaporated, dispersed in benzene and freeze-dried to provide 25 (0.5020 g, 60 ) as white strong. IR (Nujol): 3335, 1730 br, 1690, 1608, 1207 cm-1; 1H NMR (CDCl3, 200 MHz) 1.23 (br s, 30H), 1.62 (m, 8H), 2.34 (br s, 5H), 2.93 (t, 2H, J = 7.two Hz), 3.16 (br m, 2H), 3.35 (br s, 9H), three.80 (m, 2H), 4.06?.12 (m, 2H), four.25?.40 (m, 5H), four.35 (m, 2H), five.09 (m, 1H), five.20 (m, 1H), six.15 (s, 1H), 7.07?.42 (m, 7H), 7.58 (d, 2H, J= 7.3 Hz), 7.75 (d, 2H, J= 7.three Hz). 13C NMR (CDCl3, 50 MHz) 18.4, 24.six, 25.6, 26.7, 28.four, 28.5, 28.eight, 29.0, 29.two, 29.4, 29.9, 32.0, 33.8, 41.0, 47.two, 54.3, 59.three, 64.1, 65.7, 66.4, 72.2, 113.5, 116.8, 119.8, 122.8, 124.4, 124.9, 126.9, 127.5, 141.1, 143.9, 152.2, 153.7, 156.3, 160.6, 168.1, 173.0. 31P NMR (CDCl3, 160 MHz, pyrophosphate reference) -1.07. Rf (CHCl3/MeOH/H2O 65:25:four) 0.44. Anal. Calcd for C57H81N2O12PS?.5H2O: C, 64.69; H, 7.81; N, 2.65 Identified: C, 64.75; H, 7.62; N, three.16. MS MH+ C57H81N2O12PSH Calcd: 1049.5326, Located: 1049.5314. []D20 -2.4?(c 0.78, CHCl3/ MeOH four:1). 4.5.3. 2-((12-(7-(diethylamino)-2-oxo-2H-chromene-3carboxamido)dodecanoyl)oxy)-3-((12-((4-methyl-2-oxo-2H-chromen-7yl)thio)dodecyl)oxy)-3-oxopropyl phosphocholine (26)–To a option of 25 (0.1309 g, 0.125 mmol) in five mL CHCl3 was added DBU (0.1021 g, 0.66 mmol), as well as the reaction mixture was stirred at room temperature for 1 h, when cleavage of your FMOC defending group was completed. To this answer was then added p-nitrophenyl ester of 7N,N-diethylaminocoumarin-3-carboxylate (0.Fmoc-β-HoGlu(OtBu)-OH Chemical name 095 g, 0.25 mmol) and DMAP (30 mg, 0.25 mmol). The reaction was stopped immediately after 4 h, when the adverse ninhydrin test indicated that acylation of your chain-terminal amino group reached completion. The mixture was loaded straight on a silica gel column packed with CHCl3 and eluted with CHCl3/MeOH (four:1) to take away the impurities, then with CHCl3/MeOH/H2O (65:25:four). The fractions containing the product were combined, evaporated, dispersed in benzene and freeze-dried to provide 26 (87.eight mg, 66 ) as yellow strong. IR (CHCl3): 3331, 1732 br, 1598, 1208 cm-1; 1H NMR (CDCl3, 200 MHz) 1.25 (br s, 36H), 1.61 (m, 8H), two.39 (br s, 5H), two.97 (t, 2H, J = 7.2 Hz), three.36 (br m, 16H), 3.80 (m, 2H), 4.10 (m, 2H), four.20?.35 (m, 4H), 5.22 (m, 1H), six.18 (s, 1H), six.46 (s, 1H), six.65 (d, 1H, J = 6.eight Hz), 7.Buy891724-25-7 09?.PMID:24381199 47 (m, 5H), 8.76 (s, 1H), eight.78 (m, 1H). 13C NMR (CDCl3, 50 MHz) 12.4, 18.five, 24.7, 25.7, 27.0, 28.four, 28.6, 28.8, 29.1, 29.two, 29.three, 29.5, 32.1, 33.eight, 39.six, 45.0, 54.5, 59.3, 64.2, 65.7, 66.five, 72.1, 96.5, 108.three, 109.9, 110.four, 113.6, 116.8, 122.eight, 124.five, 131.0, 143.eight, 147.9, 152.three, 153.8, 157.five, 160.7, 162.7, 168.2,Tetrahedron. Author manuscript; offered in PMC 2015 Could 13.Rosseto and HajduPage173.0. 31P NMR (CDCl3, 160 MHz, pyrophosphate ref. ext.) -1.11. Rf (CHCl3/ MeOH/H2O 65:25:four) 0.45. Anal. Cald for C56H86N3O13PS?H2O: C, 60.68; H, eight.18; N, three.79 Found: C, 60.83; H, 7.83; N, 3.88. MS [M-H]+ C56H86N3O13PS-H+ Calcd: 1070.5540, Discovered: 1070.5573. []D20 -3.7?(c 0.81, CHCl3/MeOH four:1). 4.five.4. 3-((12-((4-methyl-2-oxo-2H-chromen-7-yl)thio)dodecyl)oxy)-2-((12-((1pyrrolidinyloxy-3-carboxy)dodecyl)oxy)-3-oxopropyl phosphocholine (27)– Yield: 52 . IR (CHCl3): 3349, 1739 br, 1210m cm-1; Rf (CHCl3/MeOH/H2O 65:25:four) 0.50. Anal. Cald for C51H85N3O12PS?/2H2O: C, 59.92; H, eight.68; N, 4.11 Located: C, 60.09; H, eight.69; N, three.82. MS MH+ C51H85N3O12PSH Calcd: 995.5664, Identified: 995.5715. []D20 -3.9?(c 0.92, CHCl3/MeOH four.