Combined, evaporated re-dissolved in benzene, and freeze-dried to give 12 (1.8376 g, 68.2 ) as a colorless oil that turned into a white waxy-solid. IR (CHCl3): 3300, 1738 br, 1710 br, 1614 cm-1; 1H NMR (CDCl3, 200 MHz) 1.26 (br s, 16H), 1.66 (m, 4H), two.39 (s, 3H), 2.97 (t, 2H, J = 7.two Hz), 4.16 (t, 2H, J = six.8 Hz), four.48 (m, 3H), 4.65 (s, 2H), six.19 (s, 1H), six.87?.47 (m, 8H). 13C NMR (CDCl3, 50 MHz) 18.5, 25.6, 28.4, 28.6, 28.eight, 29.1, 29.4, 29.4, 32.1, 61.9, 65.0, 65.9, 66.5, 69.0, 113.six, 113.7, 114.six, 116.8, 121.eight, 122.9, 124.four, 129.5, 143.7, 152.2, 153.8, 157.six, 160.7, 168.six, 171.7. Rf (CHCl3/EtOAc 5:1) 0.33. Anal. Cald. for C33H42O8S: C, 66.20; H, 7.07; Found: C, 66.49; H, 7.25; MS MNa+ C33H42O8SNa Calcd: 621.2498, Discovered: 621.2480. []D20 -7.3?(c 0.95, CHCl3). (ii) 12-[(4-methyl-2-oxo-2H-chromen-7-yl)thio]dodecyl-3-(2-phenoxyacetoxy)-2[(tetrahydro-2H-pyran-2-yl)oxy]propanoate: To a option of 12 (2.4 g, 4 mmol) in 20 mL of CH2Cl2 had been added three,4-dihydro-2H-pyran (1.7 g, 20 mmol) and PPTS (0.three g, 1.two mmol). The reaction was over after 3 h. The mixture was then loaded directly on a silica gel column packed with CHCl3 and eluted with CHCl3:EtOAc (eight:1). The fractions corresponding for the item had been combined and evaporated, re-dissolved in benzene, and freeze-dried to give the tetrahydropyranyl solution (2.6313 g, 96 ) as white strong. IR (CHCl3): 2928, 2850, 1738 br, 1719, 1609, 1206 cm-1; 1H NMR (CDCl3, 200 MHz) 1.25 (br s, 16H), 1.68 (m, 10H), 2.38 (s, 3H), two.96 (t, 2H, J = 7.two Hz), three.48 (m, 1H), 3.85 (m, 1H), 4.13 (t, 2H, J = six.eight Hz), 4.41 (m, 1H), 4.56 (m, 2H), 4.62 (br s, 2H),four.70?.81 (m, 1H), six.18 (s, 1H), 6.86?.46 (m, 8H). 13C NMR (CDCl3, 50 MHz) 18.5, 25.1, 25.two, 25.7, 28.4, 28.6, 28.eight, 29.0, 29.1,Tetrahedron. Author manuscript; offered in PMC 2015 May well 13.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptRosseto and HajduPage29.4, 29.9, 32.04, 61.85, 62.0, 64.1, 64.9, 65.0, 65.4, 65.5, 71.eight, 73.five, 97.3, 98.4, 113.6, 113.7, 114.five, 114.6, 116.eight, 121.7, 122.eight, 124.4, 129.4, 143.7, 152.two, 153.8, 157.5, 157.six, 160.five, 168.five, 169.six. Rf (CHCl3/EtOAc five:1) 0.88. Anal. Cald for C38H50O9S?/12C6H6: C, 67.08; H, 7.38; Discovered: C, 67.07; H, 7.42; MS MNa+ C38H50O9SNa Calcd: 705.3073, Discovered: 705.3100. (iii) (14): To a resolution of 12-[(4-methyl-2-oxo-2H-chromen-7-yl)thio]dodecyl 3-(2phenoxyacetoxy)-2-[(tetrahydro-2H-pyran-2-yl)oxy]propanoate (2.5532 g, 3.73 mmol) in 8 mL mixture of CHCl3:MeOH (1:1) kept at 0?C was added tert.butylamine (2 mL, 19 mmol,). The reaction was kept at 0?C for 14 h. The mixture was purified straight by loading it on a silica gel column packed with CHCl3 and eluted with a stepwise gradient of CHCl3:EtOAc (9:1 and six:1).131726-65-3 Formula The fractions containing the product had been combined, evaporated, re-dissolved in benzene and freeze-dried to offer 14 as a white strong (1.Salicylic acid (potassium) web 9821 g, 96.PMID:25105126 7 ). IR (CHCl3): 3300, 2855, 1735 br, 1617, 1206 cm-1; 1H NMR (CDCl3, 200 MHz) 1.26 (br s, 16H), 1.65 (m, 10H), two.38 (s, 3H), 2.96 (t, 2H, J = 7.2 Hz), 3.51 (m, 1H), three.85 (m, 3H), 4.16 (t, 2H, J = 6.eight Hz), 4.20?.40 (m, 1H), four.65?.81 (m, 1H), 6.18 (s, 1H), 7.ten?.46 (m, 3H). 13C NMR (CDCl3, 50 MHz) 18.five, 18.7, 25.1, 25.7, 28.4, 28.six, 28.eight, 29.0, 29.1, 29.4, 30.two, 30.3, 32.0, 62.6, 62.7, 62.9, 65.1, 65.2, 75.9, 77.two, 98.five, 98.8, 113.6, 116.8, 122.8, 124.4, 143.7, 152.2, 153.eight, 160.6, 170.4, 170.eight. Rf (CHCl3/EtOAc five:1) 0.25. Anal. Cald for C30H44O7S: C, 65.66; H, 8.08; Discovered: C, 65.89; H, 8.13. MS MNa+ C30H44O7SNa Calcd: 571.2705, Located: 5.