. The fractions corresponding to the item had been combined, evaporated, and dispersed in benzene and freeze-dried to give an further crop of ten (0.6398 g, 26 ) to a combined yield of 89 . IR (CHCl3): 3380 br, 1683br cm-1; 1H NMR (CDCl3+CD3OD, 200 MHz) 0.82 (br t, 3H), 1.20 (br s, 18H), 1.45 (m, 2H), three.19 (t, 2H, J= 7.32 Hz), 3.37 (br s, 2H) 3.70 (m, 2H), 4.01 (br t, 1H). 13C NMR (CDCl3, 50 MHz) 14.0, 22.five, 26.two, 27.0, 29.1, 29.2, 29.four, 29.five, 30.6, 31.eight, 38.8, 67.9, 75.0, 170.7. Rf (CHCl3/EtOAc 1:1) 0.21. Anal. Calcd for C15H31NO3 HCl3: C, 58.80; H, 10.08; N, .47; Found: C, 58.83; H, 9.77; N, four.96. MS MH+ C15H31NO3H Calcd: 274.2382, Discovered: 274.2378. []D20 -9.four?(c 1.01, CHCl3/MeOH 4:1). Process A: two) Protection of the major hydroxyl group of glyceric acid derivatives via tritylation 4.two.four. Dodecyl 2-hydroxy-3-(trityloxy)propanoate (11): To a option of 9a (1.3502 g, 4.six mmol) in 30 mL of CH2Cl2 had been added collidine (0.64 mL, four.8 mmol) and trityl chloride (1.4003 g, four.8 mmol). The reaction was kept at area temperature for 26 h. The volume of the remedy was decreased to one-third by evaporation and it was then loaded onto a silica gel column and eluted with CHCl3. The fractions corresponding towards the product were combinedTetrahedron. Author manuscript; offered in PMC 2015 Could 13.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptRosseto and HajduPageand evaporated, dissolved in benzene and freeze-dried to provide 11 (1.9008g, 80.4 ) as a white waxy strong. IR (CHCl3): 3370, 1736 cm-1; 1H NMR (CDCl3, 200 MHz) 0.88 (br t, 3H), 1.25 (br s, 18H), 1.58 (m, 2H), 3.25 (d, 1H, J = 9.four Hz), three.33 (dd, 1H, J = three, 9.four Hz), 3.49 (dd, 1H, J = three, 9.4 Hz), 4.17 (t, 2H, six.7 Hz), 4.26 (br m, 1H), 7.18?.44 (m, 15H). 13C NMR (CDCl3, 50 MHz) 14.1, 22.6, 25.7, 28.5, 29.two, 29.3, 29.4, 29.six, 31.9, 65.3, 65.9, 70.7, 86.3, 127.0, 127.eight, 128.3, 143.six, 173.two. Rf (CHCl3) 0.55. Anal. Calcd for C34H44O4?CHCl3: C, 77.83; H, eight.45; Found: C, 77.85; H, eight.40; MS MNa+ C34H44O4Na Calcd: 539.3137, Found: 539.3125. []D20 -5.7?(c 1.13, CHCl3/MeOH 4:1). 4.2.5. N-Dodecyl-2-hydroxy-3-(trityloxy)propanamide (15): To a solution of ten (0.5547 g, two mmol) in 35 mL of CHCl3 had been added trityl chloride (1.Price of (S)-3-Phenylmorpholine 0201 g, 3.Buy4-Chloro-1H-indole-7-carboxylic acid 66 mmol) and pyridine (0.PMID:23008002 5 mL), and the reaction was kept beneath reflux for 24 h. The mixture was then directly loaded on a silica gel column packed with CHCl3 and eluted with CHCl3:EtOAc (9:1). The fractions containing the item were combined, evaporated, as well as the residue redissolved in benzene and freeze-dried to offer the solution 15 (0.7427 g, 72 ) as a white waxy strong. IR (CHCl3): 3340 br m, 1657, 1236 cm-1; 1H NMR (CDCl3, 200 MHz) 0.90 (br t, 3H), 1.27 (br s, 18H), 1.48 (m, 2H), three.30 (m, 4H), four.14 (dd, 1H, J = 5.four, 9.four Hz), four.16 (m, 1H), 6.81 (m, 1H), 7.25?.45 (m, 15H). 13C NMR (CDCl3, 50 MHz) 14.1, 22.7, 26.9, 29.three, 29.two, 29.four, 29.five, 29.6, 29.7, 29.6, 31.9, 39.3, 65.0, 70.four, 87.three, 127.3, 127.9, 128.9, 129.0, 128.five, 143.3, 171.5. Rf (CHCl3/EtOAc 4:1) 0.78. Anal. Calcd for C34H45NO3. H2O: C, 77.38; H, 8.85; N, two.65; Found: C, 77.06; H, eight.82; N, 2.78. MS MNa+ C34H45NO3Na Calcd: 538.3297, Discovered: 538.3317. []D20 -2.4?(c 0.91, CHCl3/MeOH 4:1). Technique A: three) Acylation at the secondary hydroxyl group and detritylation to produce compounds 13 and 17 four.2.six. 1-(Dodecyloxy)-3-hydroxy-1-oxopropan-2-yl10-(4-methyl-2-oxo-2Hchromen-7-yl)thio)decanoate (13) (i) 1-(Dodecyloxy)-1-oxo-3-(trityloxy)propan-2-yl10-[(4-methyl-2-oxo-2H-chromen-7yl)thio]decanoate: To a so.