13-acetyl-9(R)-dihydrobaccatin III 7,9-thionocarbonate | 162743-81-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 13-acetyl-9(R)-dihydrobaccatin III 7,9-thionocarbonate
• 英文别名: [(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12,15-triacetyloxy-17-hydroxy-14,19,20,20-tetramethyl-9-sulfanylidene-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
• CAS: 162743-81-9
• 化学式: C₃₄H₄₀O₁₂S
• 分子量: 672.75
• InChiKey: VLLGFKFYSUFHKY-JZNYTDQOSA-N

物化性质

• 沸点：
  692.4±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  13-acetyl-9(R)-dihydrobaccatin III 7,9-thionocarbonate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 44.0h， 生成 [(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12-diacetyloxy-15,17-dihydroxy-14,19,20,20-tetramethyl-9-sulfanylidene-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
  参考文献：
  名称：

  Antitumor Activity of 9(R)-Dihydrotaxane Analogs

  摘要：

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.

  DOI：

  10.1021/jm00009a009
• 作为产物：
  描述：

  13-乙酰基-9-羟基巴卡丁 III 、 N,N'-硫羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以93%的产率得到13-acetyl-9(R)-dihydrobaccatin III 7,9-thionocarbonate
  参考文献：
  名称：

  Antitumor Activity of 9(R)-Dihydrotaxane Analogs

  摘要：

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.

  DOI：

  10.1021/jm00009a009

文献信息

• Synthesis of 9-deoxotaxane analogs
  作者：Larry L. Klein、Clinton M. Yeung、Leping Li、Jacob J. Plattner

  DOI：10.1016/s0040-4039(00)76947-4

  日期：1994.7

  The synthesis of 9-deoxotaxol (9) ,7,9-dideoxy and 7,9,10-trideoxygenated analogs is described starting from 13-acetyl-9(R)-dihydrobaccatin III.