Synthesis of a 2-Hydroxy-oxolane Derivative as a New Potential Crosslinking Agent of DNA

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• Compound 4 : C15H25O4Br MS (CI): 351.3 (MH+), calc. M = 350.09; 1H-NMR(200MHz. CDCl3): d 5.5 (1H,m,H-2), 5.0) (2H,m,H-1), 4.11 (4H,q J=7 Hz. Et-O) 3.32(2H,t J=6.6 Hz, CH 2-Br). 2.57 (2H, broad d,H-3) 1.85–1.34 (8H, broad m), 1.18 (6H, t, J=7 Hz Et-O); 13C-NMR(50.32. MHz.CDCl3). d 171.00, 132.36, 118.75, 61.05, 57.10, 36.79, 33.19, 32.21, 28.15, 22.87, 14.00. Compound 5: C13H21O2N MS (EIHR): 223, 1592 (M), calc, M = 223.1572; 1H-NMR(200MHz, CDCl3); d 5.61(1H,m,H-2), 4,90 (2H,m,H-1) 4.0 (2H,q,J=7 Hz. Et-O), 2.21 (2H.t J=7.1 Hz.CH 2CN) 1.55–1.21 (broad m,alkylchain); 13C-NMR(50.32 MHz.CDCl3): d 174.96, 135.00, 119.35, 116.40, 59.80, 44.74, 36.18, 30.96, 28.12, 26.06, 24.82, 13.99. Compound 7: 1H-NMR(200MHz, CDC13): d 7.44 (NH), 5.68 (1H,m,H-2), 4.90.(2H, m.H_1), 3.42 (2H. broad d.H-3), 3.20 (2H,broad q.CH 2NH), 2.26(2H,t,H-3), 1.5–1.15 (11H,m); 13C-NMR(50.32 MHz,CDCl3): d 157.30(q, J=36.7 Hz, 2JC-F), 136.83, 115.50(q, J=286.8 Hz, 1JC-F), 115.97. 65.06. 40.14, 39.83, 29.90, 29.00. 28.30, 26.24; Compound 2: C12H20NO3F3 MS(CI): 266.2 (M-18, H+); 1H-NMR(200MHz, CDCl3); d 7.28 (1H.t.NH), 5.41 (1H,m,H-2), 4.29 (1H,bd, OH), 4.04, 3.84, 3.48, 3.31 (2H,4t,H-5) 3.20 (2H.q.CH2 NH). 1.90–1.15 (13H,multiplets); 13C-NMR (50.32 MHz,DMSO-d6): d 157.30 (q.2JC-F=36.7 Hz), 115.81 (q. 1JC-F,=286.8 Hz,) 98.87 (C-2), 98.38 (C-2), 72.64 (C-5), 71.79 (C-5). 39.80, 38.71 (C-4), 36.47 (C-4), 33.35, 33.07, 32.71, 29.04, 28.59, 28.22, 28.10, 27.10, 26.40. Compound 8: C12H20NO3F3 MS(CI) :389.0 (MH+) cacl, M=388.20 NMR(200MHz, CDCl3): d 6.80(NH), 6.35(1H,d,H-Pyrimidine)), 5.99(1H,m,H-2), 5.5(1H,bt,NH), 3.99–3.90 and 3.43–3.39 (2H,m,H-5) 3.34 (2H,bq, CH2 NH)2.35(1H,m), 2.24 (6H,s,CH3.C-7′,8′) 1.88–1.27(12H,multiplets): 13C-NMR(50.32 MHz,DMSO-d6): d 167.56, 161.20, 157.00(q, 2JC-F=36.6 Hz,), 115.80 (q. J=286.8 Hz, 1JC-F,), 111.26 and 111.18(C-5′). 82.76 and 82.30(C-2), 71.20 and 71.11(C-5), 39.79, 39.25, 39.00, 38.28, 38.03, 32.97, 32.55, 29.06, 28.73, 28.18, 28.03, 26.45, 23.72.
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