A New Deoxygenation Method for Taxanes Using Hypophosphorous Acid
被引量：1
A New Deoxygenation Method for Taxanes Using Hypophosphorous Acid
参考文献9
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7 [7]Selected data of 14-deoxy-SIA: white solid, [α]+54 (c 0.83, CHCl3); mp: 128.5-131.2℃; 1H NMR (500MHz, CDCl3, δ ppm): 6.06 (dd,1H, J=5.3Hz,12.3Hz, H-10), 5.38 (dd,1H, J=2Hz, 6.3Hz, H-2), 5.27(t, 1H, J=3Hz, H-5), 5.25 (s, 1H, H-20), 4.89 (s, 1H, H-20), 3.08(d,1H, J=6Hz, H-3), 2.45 (m, 1H, H-13), 2.37 (dd, 1H, J=12Hz, 14.5Hz, H-9), 2.12 (s, 3H, OAc-CH3-10), 2.06 (s, 3H, CH3-18), 2.04 (s, 3H, OAc-CH3-2), 2.03 (s, 3H, OAc-CH3-4), 2.09-1.87 (m 3H, H-7, H-13, H-14), 1.80 (m, 3H, H-1, 2×H-6), 1.68 (m, 1H, H-14), 1.59 (s, 3H, CH3-16), 1.58 (m, 1H, H-9), 1.22(m, 1H, H-7),1.05 (s, 3H, CH3-17), 0.85 (s, 3H, CH3-19); 13CNMR (125MHz, CDCl3, δ ppm): 170.18 (OAc-C=O), 169.63 (OAc-C=O), 169.62 (OAc-C=O), 144.35 (C-4), 136.96 (C-12), 133.90 (C-11), 116.36 (C-20), 78.73 (C-5), 72.25 (C-2), 70.49 (C-10), 52.01 (C-1), 43.78 (C-9), 41.19 (C-3), 39.68 (C-8), 37.09 (C-15), 33.65 (C-7), 31.67 (C-17), 30.10 (C-13), 28.96 (C-6), 25.33 (C-16), 22.50 (19-CH3), 22.01 (OAc-CH3), 21.66 (OAc-CH3), 21.65 (OAc-CH3), 21.22 (18-CH3), 18.29 (C-14); FABMS: m/z 447.3(M+1).
8 [8]Selected data of compound 3: white solid, [α]+83 (c 0.54, CHCl3); mp 198-200℃; 1HNMR(500MHz, CDCl3, δ ppm): 7.97(dt, 2H, J=7.7Hz, 1.5Hz, Bz), 7.58(t, 1H, J=7.5Hz, Bz), 7.46(t, 2H, J=7.5Hz, Bz), 6.00(dd, 1H, J=12.3Hz, 5.5Hz, H-10), 5.77(dd, 1H, J=5.7Hz, 2.5Hz, H-2), 4.75(dd, 1H, J=9.2Hz, 3.0Hz, H-5), 4.31(d, 1H, J=8.0Hz, H-20), 4.16(d, 1H, J=8.0Hz, H-20), 2.47(dd, 1H, J=14.5Hz, 12.5Hz, H-9), 2.42(m, 1H, H-13), 2.26(d, 1H, J=6Hz, H-3), 2.11(m, 2H, H-6, H-13), 2.06(s, 3H, OAc-CH3-10), 1.97(m, 1H, H-6), 1.90(s, 3H,CH3-18), 1.86(m, 1H, H-1), 1.67(s, 3H, CH3-16), 1.63(m, 1H, H-7), 1.33(s, 3H, CH3-19), 1.07(s, 3H, CH3-17); 13C NMR (125MHz, CDCl3, δ ppm): 170.12(10-OAc-C=O), 165.34(2-Bz-C=O), 137.81(C-12), 134.43(C-11),133.34, 129.58, 129.48, 128.65(6xph), 87.56(C-5), 80.52(C-4), 76.24(C-20), 73.43(C-10), 70.50(C-2), 50.23(C-1), 46.01(C-9), 44.85(C-3), 37.21(C-8), 36.51(C-15), 35.03(C-17), 32.35(C-13), 29.60(C-7), 27.22(C-6), 25.12(C-16), 21.76(C-19), 21.51 (OAc-CH3), 21.13(C-18), 18.18(C-14); FABMS: m/z 483.4(M+1).
9 [9]Reaction procedure: The solution of compound 1 , triethyl amine(5eq), 50% hypophosphorous acid(5eq) and cyclohexene(5eq) in dioxane under argon was treated with AIBN(0.1eq) solution ( 0.1 mol/L in dioxane) for several times ( at every 30 min) under reflux. The solution was washed with water and dried over anhydrous NaSO4, concentrated and chromatographed to give 14-deoxy-SIA.
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