2,3,6,2',3',4',6'-hepta-O-pivaloyl-D-cellobiose-1-α-trichloroacetimidate | 676144-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6,2',3',4',6'-hepta-O-pivaloyl-D-cellobiose-1-α-trichloroacetimidate
• 英文别名: pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]Glc(b1-4)[pivaloyl(-2)][pivaloyl(-3)][pivaloyl(-6)]Glc(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-bis(2,2-dimethylpropanoyloxy)-6-(2,2,2-trichloroethanimidoyl)oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 676144-18-6
• 化学式: C₄₉H₇₈Cl₃NO₁₈
• 分子量: 1075.51
• InChiKey: JYWWKEIGCHMJIJ-NVQDZEKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  71
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  ICI 182,780-3-benzoate 、 2,3,6,2',3',4',6'-hepta-O-pivaloyl-D-cellobiose-1-α-trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 以78%的产率得到[(7R,8R,9S,13S,14S,17S)-17-[(2R,3R,4S,5R,6R)-3,4-bis(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-(2,2-dimethylpropanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-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
• 作为产物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-pivaloyl-D-cellobiose 在 caesium carbonate 作用下， 生成 2,3,6,2',3',4',6'-hepta-O-pivaloyl-D-cellobiose-1-α-trichloroacetimidate
  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