(2aS,2bR,3S,4S,6S,8aR,11aS,11bS,12S,13aR)-2a-acetoxy-4,6-dihydroxy-12-methoxy-7,10,10,11b,14,14-hexamethyl-2a,2b,3,4,5,6,8a,11a,11b,12,13,13a-dodecahydro-2H-4,8-methanooxeto[3'',2'':3',4']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-3-yl benzoate | 478161-69-2

• 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: (2aS,2bR,3S,4S,6S,8aR,11aS,11bS,12S,13aR)-2a-acetoxy-4,6-dihydroxy-12-methoxy-7,10,10,11b,14,14-hexamethyl-2a,2b,3,4,5,6,8a,11a,11b,12,13,13a-dodecahydro-2H-4,8-methanooxeto[3'',2'':3',4']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-3-yl benzoate
• CAS: 478161-69-2
• 化学式: C₃₃H₄₄O₁₀
• 分子量: 600.706
• InChiKey: CNOBRAGWRLIYIB-GQMMPTOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  43.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  129.98
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2aS,2bR,3S,4S,6S,8aR,11aS,11bS,12S,13aR)-2a-acetoxy-4,6-dihydroxy-12-methoxy-7,10,10,11b,14,14-hexamethyl-2a,2b,3,4,5,6,8a,11a,11b,12,13,13a-dodecahydro-2H-4,8-methanooxeto[3'',2'':3',4']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-3-yl benzoate 在 sodium hexamethyldisilazane 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 [(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-16-hydroxy-18-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyridin-4-ylpropanoyl]oxy-8-methoxy-4,4,7,19,20,20-hexamethyl-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. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5
• 作为产物：
  描述：

  在 氟化氢吡啶 作用下， 以 吡啶 为溶剂， 以85%的产率得到(2aS,2bR,3S,4S,6S,8aR,11aS,11bS,12S,13aR)-2a-acetoxy-4,6-dihydroxy-12-methoxy-7,10,10,11b,14,14-hexamethyl-2a,2b,3,4,5,6,8a,11a,11b,12,13,13a-dodecahydro-2H-4,8-methanooxeto[3'',2'':3',4']benzo[1',2':3,4]cyclodeca[1,2-d][1,3]dioxol-3-yl benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5