methyl (1S,5S,7R)-7-((tert-butyldimethylsilyl)oxy)-8-methyl-3-(((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate | 948890-18-4

• 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: methyl (1S,5S,7R)-7-((tert-butyldimethylsilyl)oxy)-8-methyl-3-(((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 948890-18-4
• 化学式: C₂₆H₄₁NO₇Si
• 分子量: 507.7
• InChiKey: TWPJVGXMAUNSER-PBUIHYCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,5S,7R)-7-((tert-butyldimethylsilyl)oxy)-8-methyl-3-(((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium amalgam 、 硫酸 、 四丁基氟化铵 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Positional linker effects in haptens for cocaine immunopharmacotherapy

  摘要：

  Cocaine use remains a serious problem, despite intensive efforts to curb abuse. Given the lack of effective pharmacotherapeutics for the treatment of cocaine addiction, research groups have targeted immunopharmacotherapy in which the drug user's immune system is trained to recognize and remove cocaine prior to entry into the central nervous system. Antibody cocaine esterases and simple binders have been procured, however, rates and/or affinities still need improvement before clinical trials are warranted. Herein, we report the synthesis and testing of two new haptens for the procurement of cocaine binding antibodies and cocaine esterase catalytic antibodies. Central in the design of these haptens was the placement of the linker functionality distal from the anticipated cocaine epitopes in an attempt to bury the hapten deep within an antibody combining site to gain possible entropic and enthalpic advantages. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.032
• 作为产物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (+/-)-7β-(tert-butyldimethylsilyloxy)-2β-(methoxycarbonyl)tropan-3-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到methyl (1S,5S,7R)-7-((tert-butyldimethylsilyl)oxy)-8-methyl-3-(((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)oxy)-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Positional linker effects in haptens for cocaine immunopharmacotherapy

  摘要：

  Cocaine use remains a serious problem, despite intensive efforts to curb abuse. Given the lack of effective pharmacotherapeutics for the treatment of cocaine addiction, research groups have targeted immunopharmacotherapy in which the drug user's immune system is trained to recognize and remove cocaine prior to entry into the central nervous system. Antibody cocaine esterases and simple binders have been procured, however, rates and/or affinities still need improvement before clinical trials are warranted. Herein, we report the synthesis and testing of two new haptens for the procurement of cocaine binding antibodies and cocaine esterase catalytic antibodies. Central in the design of these haptens was the placement of the linker functionality distal from the anticipated cocaine epitopes in an attempt to bury the hapten deep within an antibody combining site to gain possible entropic and enthalpic advantages. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.032