[(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-17-[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate | 676144-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-17-[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 676144-17-5
• 化学式: C₆₅H₉₃F₅O₁₃S
• 分子量: 1209.5
• InChiKey: WVFSXOMXHFUTFY-HJUCEDTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  84
• 可旋转键数：
  32
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-17-[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate 在 四乙基氢氧化铵 作用下， 以 水 、 异丙醇 为溶剂， 反应 9.0h， 以65%的产率得到17-β-D-glucosylfulvestrant
  参考文献：
  名称：

  Sugar conjugates of fulvestrant (ICI 182,780): efficient general procedures for glycosylation of the fulvestrant core

  摘要：

  We have prepared glucose and cellobiose conjugates at the phenolic 3- and hydroxylic 17-positions of the pure antiestrogenic compound fulvestrant (ICI 182,780), which has recently been approved in the USA for the treatment of advanced postmenopausal breast cancer. Glycosylation at the 17-position was achieved most effectively using pivaloyl protection of the sugar imidates employed, which we found suppressed the competing transacylation reaction and led to improved yields of the product glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.140
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-pivaloyl-D-glucopyranose 在 三氟化硼乙醚 、 caesium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 172.75h， 生成 [(7R,8R,9S,13S,14S,17S)-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-17-[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate
  参考文献：
  名称：

  Sugar conjugates of fulvestrant (ICI 182,780): efficient general procedures for glycosylation of the fulvestrant core

  摘要：

  We have prepared glucose and cellobiose conjugates at the phenolic 3- and hydroxylic 17-positions of the pure antiestrogenic compound fulvestrant (ICI 182,780), which has recently been approved in the USA for the treatment of advanced postmenopausal breast cancer. Glycosylation at the 17-position was achieved most effectively using pivaloyl protection of the sugar imidates employed, which we found suppressed the competing transacylation reaction and led to improved yields of the product glycosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.140