L. Calcd for C25H51N2O7P 2O: C, 55.54; H, 9.88; N, 5.18; Found: C, 55.18; H, 9.83; N, 5.14. MS MH+ C25H51N2O7PH+ Calcd: 523.3512, Located: 523.3503. four.3.4. 3-[(12-(7-mercapto-4-methylcoumarin-7yl)dodecyloxy]-3-oxo-2[(tetrahydro-2H-pyran-2-yl)oxy]propyl phosphocholine (23)–To a solution of 14 (0.9651 g, 1.76 mmol) in 30 mL benzene in an ice-bath were added 2-chloro-2-oxo-1,two,3dioxaphospholane (0.32 mL, three.five mmol) followed by triethylamine (0.5 mL, three.five mmol) dropwise. Following the addition of NEt3, the ice-bath was removed and also the reaction was left stirring at area temperature for 4 h. The mixture was filtered and the crystalline precipitate of triethylamine hydrochloride was removed. The solvent was evaporated and also the oily residue was dissolved in 45 mL of anhydrous acetonitrile, the resulting solution was transferred to a pressure bottle and frozen to -10 . To this frozen remedy was added excess trimethylamine (five mL), the stress bottle was then sealed and heated to 65 for 24 h. Following that the mixture was cooled to area temperature, and then kept at 7 overnight, when a white precipitate formed. The precipitate was separated in the acetonitrile option, which was then evaporated to offer an oily residue. Each samples have been purified by silica gel chromatography employing separate columns, packed with CHCl3/MeOH (4:1) and eluted with In each cases, with CHCl3/MeOH/H2O (65:25:four) The fractions corresponding for the product have been isolated, evaporated, dispersed in benzene and freeze-dried to give 23 as a white solid (all round yield: 0.9217 g 74 , from precipitate 0.7201 g, and in the MeCN phase 0.2016 g). IR (CHCl3): 3350, 2852, 1732, 1621, 1207 cm-1; 1H NMR (CDCl3, 200 MHz) 1.27 (br s, 16H), 1.66 (m, 10H), two.39 (s, 3H), two.97 (t, 2H, J = 7.two Hz), 3.36 (br s, 9H), 3.80 (m, 6H), 4.ten (t, 2H, J = six.8 Hz), 4.31 (m, 3H), 4.80 (m, 1H), 6.19 (s, 1H), 7.12?.43 (m, 3H). 13C NMR (CDCl3, 50 MHz) 18.five, 19.1, 25.two, 25.8, 25.9, 28.5, 28.six, 28.9, 29.1, 29.3, 29.five, 32.1, 54.three, 59.4, 62.three, 65.two, 66.two, 98.9, 113.7, 116.9, 122.9, 124.23405-32-5 Purity five, 143.Price of Burgess reagent 8, 152.PMID:24318587 2, 153.8, 160.six, 170.7. 31P NMR (CDCl3, 160 MHz, pyrophosphate external reference) -1.71 and -1.07. Rf (CHCl3/MeOH/H2O 65:25:four) 0.31. Anal. Cald for C35H56NO10PS?H2O HCl3: C, 49.74; H, 7.07; N, 1.61 Located: C, 49.77; H, 7.07; N, 1.52. MS MNa+ C35H56NO10PSNa Calcd: 736.3260, Discovered: 736.3239.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron. Author manuscript; available in PMC 2015 Could 13.Rosseto and HajduPage4.4. Basic procedure for hydrolytic cleavage in the tetrahydropyranyl protecting group to create the lysophospholipid analoguesNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript4.4.1. 3-(Dodecylamino)-2-hydroxy-3-oxopropyl phosphocholine (22)–To a cloudy resolution of 21 (0.3521 g, 0.67 mmol) in 25 mL 1,4-dioxane was added 0.15 mL 12 M aq. HCl. The reaction mixture was stirred at room temperature for two h. In the finish with the reaction 30 mL dioxane was added, and then the reaction mixture was freeze-dried. The white residue obtained was dissolved in CHCl3/MeOH/H2O (65:25:4) and purified on a quick silica gel column packed with CHCl3 and eluted with CHCl3/MeOH/H2O (65:25:four). The fractions containing the item have been collected, evaporated, dispersed in benzene and freeze-dried to offer 22 (0.2762 g, 94 ) as white strong. IR (CHCl3): 3352, 1675 cm-1; 1H NMR (CDCl3, 200 MHz) 0.86 (br t, 3H), 1.24 (br s, 16H), 1.52 (m, 2H), 3.33 (br s, 13H), three.72 (m, 3H), four.21 (m,.