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Regioselective protection of 10-deacetylbaccatin Ⅲ and semi-synthesis of paclitaxel

Regioselective protection of 10-deacetylbaccatin Ⅲ and semi-synthesis of paclitaxel
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摘要 Semi-synthesis of paclitaxel was achieved in four steps from 10-deacetylbaccatin HI （10-DAB HI）. The key steps are the regioselective protection at the hydroxyl group at C-7 of 10-DAB HI, using 1,1′-thiocarbonyldiimidazole as a selective reagent, and the deprotection of the protected paclitaxel with a mixture of p-toluenesulfonic acid and 0.1 mol/L aqueous hydrochloride. Semi-synthesis of paclitaxel was achieved in four steps from 10-deacetylbaccatin HI （10-DAB HI）. The key steps are the regioselective protection at the hydroxyl group at C-7 of 10-DAB HI, using 1,1′-thiocarbonyldiimidazole as a selective reagent, and the deprotection of the protected paclitaxel with a mixture of p-toluenesulfonic acid and 0.1 mol/L aqueous hydrochloride.
作者 Zhang Hu Li Li Ou Guo Lin Zhang Yong Ping Yu
机构地区 College of Pharmaceutical Science College of Science
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2008年第2期130-132,共3页 中国化学快报（英文版）
关键词 PACLITAXEL Protecting group 1 1′-Thiocarbonyldiimidazole REGIOSELECTIVE SEMI-SYNTHESIS Paclitaxel Protecting group 1,1′-Thiocarbonyldiimidazole Regioselective Semi-synthesis
分类号 TQ17 [化学工程—硅酸盐工业]
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参考文献11

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  • 8[8]Data of compound 3:m.p.145-148 (C;IR (KBr)(:3445,2955,1717,1285,1245,973,742 cm-1;1H NMR (400 MHz,DMSO-d6,δ ppm):8.31 (s,1H),8.05 (d,2H,J = 7.2 Hz),7.69 (m,1H),7.67 (s,1H),7.58 (dd,2H,J = 8.0,7.2 Hz),7.09 (s,1H),6.11 (dd,1H,J = 9.2,8.4 Hz),5.51(d,1H,J = 6.8 Hz),5.29 (d,1H,J = 4.4 Hz),5.24 (s,1H),5.18 (s,1H),5.02 (d,1H,J = 9.2 Hz),4.63 (s,1H),4.46 (s,1H),4.14 (s,2H),4.04 (d,1H,J=6.8 Hz),2.73 (m,1H),2.25 (s,3H),2.21 (m,2H),1.94 (s,3H),1.90 (m,1H),1.85 (s,3H),0.96 (s,3H),0.94 (s,3H);13C NMR(100 MHz,DMSO-d6,δ ppm):209.2,182.7,170.0,165.3,141.9,136.9,134.4,133.3,130.8,130.1,129.5 (2C),128.7 (2C),118.6,82.7,81.9,79.5,76.9,75.4,74.7,74.4,69.9,55.4,46.2,42.3,39.1,31.2,26.6,22.1,20.1,14.8,11.2;LCMS calcd,for C33H38N2O10Sm/z 654.2,found 654.4.
  • 9[9]Data of compound 4:m.p.241-244 C;IR (KBr)v:3466,2943,1722,1279,1236,978,710 cm-1;1H NMR (400 MHz,DMSO-d6,δ ppm):8.15 (s,liD,8.04 (d,2H,J = 7.2 Hz),7.69 (dd,1H,J= 8.0,7.2 Hz),7.59 (t,2H,J= 7.6 Hz),7.54 (s,1H),7.03 (s,1H),6.16 (s,1H),6.12 (m,1H),5.49 (d,1H,J = 7.2 Hz),5.44 (d,1H,J = 4.4 Hz),5.05 (d,1H,J = 5.2 Hz),4.65 (s,2H),4.13 (s,2H),3.95 (d,1H,J = 7.2 Hz),2.86 (m,1H),2.25 (s,3H),2.19 (m,2H),1.95 (s,6H),1.86 (m,1H),1.84 (s,3H),0.98 (s,6H);13C NMR (100 MHz,DMSO-d6,δ ppm):202.7,183.1,170.1,168.5,165.2,146.2,136.9,133.4,130.4,130.1,130.0,129.6 (2C),128.8 (2C),118.5,82.7,81.4,79.5,76.8,75.5,75.2,74.0,66.0,55.5,46.7,42.4,39.1,31.1,26.5,22.2,20.6,20.3,15.3,11.2;LCMS calcd,for C3sH40N2O11S m/z 696.2,found 696.5.
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Chinese Chemical Letters
2008年 第2期

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