Lution of 11 (1.0012 g, 1.93 mmol) in 30 mL of CHCl3 have been added (4-methyl-7-mercaptocoumarin-7yl)-10-decanoic acid (0.7002 g, 1.93 mmol), DCC (0.4008 g, 1.93 mmol) and DMAP (50 mg, 0.41 mmol). The reaction was stopped after four h stirring at room temperature. The mixture was filtered plus the solvent was evaporated. The residue was redissolved in CHCl3 and purified on silica gel column packed with CHCl3:hexane (1;1) and eluted using a step-wise gradient of CHCl3:hexane (1:1, 7:5, two:1 and 5:1). The fractions corresponding to the product were isolated, evaporated, dissolved in benzene and freeze-dried to offer the analytically pure product (1.1903 g, 72 ) as a colorless wax. IR (CHCl3): 3340, 1735 br, 1625, 1210 cm-1; 1H NMR (CDCl3, 200 MHz) 0.91 (br t, 3H), 1.28 (br s, 28H), 1.65 (m, 6H), two.32 (s, 3H), two.50 (t, 2H, J = 7.four Hz), two.94 (t, 2H, J = six.8 Hz), 3.52 (br s, 2H), four.16 (m, 2H), 5.25 (m, 1H), 6.16 (s, 1H), 7.ten?.49 (m, 18H). 13C NMR (CDCl3, 50 MHz) 13.9, 18.2, 22.five, 24.six, 25.five, 28.3, 28.4, 28.six, 28.9, 29.0, 29.1, 29.two, 29.4, 31.7, 31.eight, 33.8, 62.9, 65.3, 71.63, 86.four, 113.four, 116.six, 122.5, 124.three, 126.9, 127.six, 128.0, 128.four, 143.3, 143.6, 151.9, 153.six, 160.two, 167.93, 172.70. Rf (CHCl3) 0.27. Anal. Cald for C54H68O7S: C, 75.31; H, 7.96; Located: C, 75.71; H, 7.66; MS MNa+ C54H68O7SNa Calcd: 883.4583, Located: 883.4575. []D20 -7.2?(c 1.21, CHCl3/MeOH four:1)Tetrahedron. Author manuscript; readily available in PMC 2015 May perhaps 13.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptRosseto and HajduPage(ii) (13): To a remedy on the product 1-(dodecyloxy)-1-oxo-3-(trityloxy)propan-2-yl-10-((4methyl-2-oxo-2H-chromen-7-yl)thio)decanoate (0.8012 g, 0.93 mmol) in 25 mL of 1,4dioxane was added a resolution of HCl (0.25 mL 1M aq. HCl diluted with five mL of 1,4dioxane). The reaction mixture was kept at room temperature overnight. To this mixture was added 30 mL benzene and then freeze-dried. The white residue obtained was dissolved in CHCl3 and purified on silica gel column packed with CHCl3 and eluted with CHCl3:EtOAc (9:1).Azido-PEG3-alcohol site The fractions containing the item have been isolated, evaporated, re-dissolved in benzene and freeze-dried to give 13 (0.Price of 979-88-4 3402 g, 61 ) as white solid.PMID:29844565 IR (Nujol): 3350, 1738 br, 1630 cm-1; 1H NMR (CDCl3, 200 MHz) 0.91 (br t, 3H), 1.26 (br s, 30H), 1.65 (m, 4H), two.35 (m, 5H), two.93 (t, 2H, J = 6.8 Hz), three.94 (br m, 2H), four.11 (t, 3H, J = six.eight Hz), five.12 (t, 1H, J = 4 Hz), 6.15 (s, 1H), 7.07?.43 (m, 3H). 13C NMR (CDCl3, 50 MHz) 14.0, 18.4, 22.five, 24.six, 25.6, 28.3, 28.5, 28.7, 28.9, 29.0, 29.1, 29.2, 29.3, 29.four, 29.5, 31.8, 32.0, 33.7, 62.0, 65,6, 73.1, 113.5, 113.6, 116.7, 122.7, 124.four, 143.7, 152.two, 153.7, 160.6, 168.two, 172.8. Rf (CHCl3/EtOAc 9:1) 0.49. Anal. Cald for C35H54O7S C6H6: C, 68.67; H, eight.76; Found: C, 68.57; H, 8.50; MS MNa+ C35H54O7S Calcd: 618.3590, Discovered: 618.3583. []D20 -8.9?(c 1.23, CHCl3/MeOH 4:1). four.2.7. 1-(dodecylamino)-3-hydroxy-1-oxopropan-2-yl10-((4-methyl-2-oxo-2Hchromen-7-yl)thio)decanoate (17) (i) 1-(Dodecylamino)-1-oxo-3-(trityloxy)propan-2-yl10-[(4-methyl-2-oxo-2H-chromen-7yl)thio]decanoate: To a resolution of 15 (0.5402 g, 1.05 mmol) in 30 mL of CHCl3 had been added (4-methyl-7-mercaptocoumarin)-10-decanoic acid (0.4567 g, 1.26 mmol), DCC (0.3362 g, 1.26 mmol) and DMAP (32 mg, 0.26 mmol, 20 mol ). The reaction was more than immediately after 1 h stirring at space temperature. The DCC-urea that formed was filtered and also the solvent was evaporated. The residue was re-dissolved in CHCl3 and purified on a silica gel column packed with C.