[(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoyl]oxy-8,16-dihydroxy-4-(4-methoxyphenyl)-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate | 184586-18-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoyl]oxy-8,16-dihydroxy-4-(4-methoxyphenyl)-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
• CAS: 184586-18-3
• 化学式: C₅₈H₇₉NO₁₆Si
• 分子量: 1074.35
• InChiKey: BVSJEEJWNZDGHV-BKYFAONHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.61
• 重原子数：
  76
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  217
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoyl]oxy-8,16-dihydroxy-4-(4-methoxyphenyl)-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate 在 吡啶 、 氢氟酸 作用下， 以68%的产率得到[(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxy-8,16-dihydroxy-4-(4-methoxyphenyl)-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-Dihydrobaccatin-9,10-acetals

  摘要：

  To synthesize new highly active taxoids, we designed and synthesized 9beta-dihydro-9,10-acetal taxoids. In vitro study of these analogues clearly showed them to be more potent than docetaxel. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00069-0
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 tetrabutylammonium borohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 [(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoyl]oxy-8,16-dihydroxy-4-(4-methoxyphenyl)-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-Dihydrobaccatin-9,10-acetals

  摘要：

  To synthesize new highly active taxoids, we designed and synthesized 9beta-dihydro-9,10-acetal taxoids. In vitro study of these analogues clearly showed them to be more potent than docetaxel. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00069-0