An Unusual Formation of Cyclic Sulfite at C-4 and C-5 Positions of Taxane
An Unusual Formation of Cyclic Sulfite at C-4 and C-5 Positions of Taxane
摘要
An unusual formation of cyclic sulfite at C-4 and C-5 positions of taxane was accomplished by treatment of compound 1 with excess MeSO2Cl/Et3N and a possible mechanism was proposed.
参考文献5
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4[4]Spectral data of compound 2: colorless film; FABMS m/z 633 (M+Na); 1H NMR (300 MHz, CDCl3, δppm) 6.05 (dd, 1H, J = 10.7 Hz, 5.7 Hz, H-10), 5.38 (d, 1H, J = 3.9 Hz, H-2), 4.49 (br.dd, 1H, H-13), 4.47 (d, 1H, J = 12.6 Hz, H-20), 4.07 (d, 1H, J = 11.7 Hz, H-20), 3.86 (t, 1H, J = 2.7 Hz, H-5), 3.06 (d, 1H, J = 5.1 Hz, H-3), 2.99 (s, 1H, OH), 2.48-2.25 (m, 3H, 2×H-14, H-9), 2.18-2.04 (4s, 12H, 3×OAc-CH3, CH3-18), 1.99-1.87 (m, 1H, H-7), 1.83-1.64 (m, 3H, 2×H-6, H-1), 1.59 (s, 3H, CH3-16), 1.42 (dd, 1H, J = 4.8 Hz, 15.3 Hz, H-9), 1.05 (m, 1H, H-7), 1.00 (t, 9H, TES-CH3), 0.98 (s, 3H, CH3-17), 0.85 (s, 3H, CH3-19), 0.66 (q, 6H, TES-CH2); Spectral data of compound 3: pale yellow film; HR - FABMS (Gly+NaCl):Found. 679.2932 calcd. 679.2942,C32H52O10SSi +Na; 1H NMR (500 MHz, CDCl3, δppm) 6.02 (dd, 1H, J = 12.5 Hz, 5.5 Hz, H-10), 5.29 (dd, 1H, J = 2 Hz, 6 Hz, H-2), 5.22 (t, 1H, J = 2.5 Hz, H-5), 4.84 (d, 1H, J = 12.5 Hz, H-20), 4.55 (dd, 1H, J = 6.5 Hz, 9.5Hz, H-13), 4.09 (d, 1H, J = 11.7 Hz, H-20), 2.45 (d, 1H, J = 5.5 Hz, H-3), 2.42-2.38 (m, 2H, H-14, H-9), 2.24-2.00 (4s+m, 15H, 3×OAc-CH3, CH3-18, H-14, H-7, 2×H-6), 1.75 (dd, 1H, J = 1 Hz, 7 Hz, H-1), 1.63 (s, 3H, CH3-16), 1.45 (dd, 1H, J = 5.5 Hz, 15 Hz, H-9), 1.29 (m, 1H, H-7), 1.01-0.98 (t+s, 12H, TES-CH3, CH3-17), 0.88 (s, 3H, CH3-19), 0.68-0.62 (m, 6H, TES-CH2);
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