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Ied to give 4 mg (90 ) 14. 1H NMR (CD3OD, four hundred MHz), four.46-4.51 (m
The solution was stirred for nine h at home Glycerol 3-phosphate MSDS temperature underneath argon. The crude compound was purified by silica gel chromatography PubMed ID:https://www.ncbi.nlm.nih.gov/pubmed/25564241 (five methanol in chloroform ) to give six mg (eighty four ) of pure fifteen. 1H NMR (CDCl3, 400 MHz), seven.70 (d, J = 7.six Hz, 2H), 7.50 (dd, J = 7.six, one.two Hz, 2H), 7.34 (dd, J = 7.six, seven.two Hz, 2H), 7.27-7.23 (ddd, J = seven.six, 7.two, one.2 Hz, 2H), six.51 (dd, J = 1.6, 2.eight Hz, 1H), five.ninety eight (dd, J = 2.eight, three.6 Hz, 1H), 5.79 (m, 1H), five.74 (m, 1H), five.fifty eight (s, 1H), 4.eighty two (s, 1H), four.40 (m, 1H), four.36 (d, J = 7.2 Hz, 2H), 4.twenty (m, 1H), 4.fifteen (t, J = seven.2 Hz, 1H), three.seventy six (t, J = 7.two Hz, 2H), 3.fifteen (m, 2H), three.05 (m, 1H), 2.84-2.seventy nine (dd, J = 4.8, 12.8 Hz, 1H), two.78-2.76 (m, 2H), two.71-2.66 (m, 2H), 2.64-2.sixty one (d, J = twelve.8 Hz, 1H), two.06-2.10 (dt, J = three.6,NIH-PA Creator Manuscript NIH-PA Writer Manuscript NIH-PA Writer ManuscriptBioorg Med Chem. Author manuscript; Reserpine mechanism of action offered in PMC 2010 November one.Lu et al.Page7.two Hz, 2H), one.72-1.36 (10H). HRMS (FAB) (m/z) calcd for C35H43N4O4S+ (MH+) 615.3005, discovered 615.2995.NIH-PA Writer Manuscript NIH-PA Writer Manuscript NIH-PA Writer Manuscript3-(1-4-[5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl-1Hpyrrol-2-yl)-propionic acid (sixteen) 5 L DBU was added to fifteen (6 mg, 0.01 mmol) in 500 L THF and stirred for 2 h. TLC (10 methanol in chloroform, Rf = 0.3) showed the completion with the reaction by disappearance of your UV energetic beginning spot. The corresponding acid was purified by flash chromatography (seven methanol in chloroform) to supply 3.seven mg (eighty five ) acid 16. 1H NMR (CD3OD, 400 MHz), six.fifty seven (dd, J = 2.eight, one.6 Hz, 1H), five.92 (dd, J = three.2, two.8 Hz, 1H), 5.79 (m, 1H), four.60 (3H), four.48 (m, 1H), four.27 (m, 1H), three.86 (t, J = seven.two Hz, 2H), 3.19-3.fifteen (3H), two.94-2.89 (dd, J = four.eight, 12.8 Hz, 1H), two.86-2.eighty two (m, 2H), two.71-2.sixty seven (d, J = twelve.8 Hz, 1H), two.60-2.fifty six (m, 2H), 2.20-2.17 (t, J = 7.two Hz, 2H), 1.72-1.36 (10H). HRMS (FAB) (m/z) calcd for C21H33N4O4S+ (MH+) 437.2222, identified 437.2193; calcd for C21H31N4O3S+ (M+-OH) 419.2117, located 419.2102. four,7-Dioxo-heptanoic acid methyl ester (DOHA-Me, 17) Ester 1 (22.five mg, 0.104 mmol) in 5 mL of AcOH/H2O (three:1, v/v) was PubMed ID:https://www.ncbi.nlm.nih.gov/pubmed/25564241 stirred at fifty for 5 h. TLC (CHCl3): Rf = 0.forty five confirmed the completion on the reaction.The solvent was taken off by rotary evaporation.
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