methyl (1R,2R,3S,5S)-8-[6-[(2-methylpropan-2-yl)oxy]-6-oxohexyl]-3-(oxido-phenyl-phenylmethoxyphosphaniumyl)oxy-8-azabicyclo[3.2.1]octane-2-carboxylate | 148533-53-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: methyl (1R,2R,3S,5S)-8-[6-[(2-methylpropan-2-yl)oxy]-6-oxohexyl]-3-(oxido-phenyl-phenylmethoxyphosphaniumyl)oxy-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 148533-53-3
• 化学式: C₃₂H₄₄NO₇P
• 分子量: 585.678
• InChiKey: SOFFNSBFOXNLGR-CJWBMGKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,3S,5S)-8-[6-[(2-methylpropan-2-yl)oxy]-6-oxohexyl]-3-(oxido-phenyl-phenylmethoxyphosphaniumyl)oxy-8-azabicyclo[3.2.1]octane-2-carboxylate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 生成 3-[6-[(1R,2R,3S,5S)-3-[hydroxy(phenyl)phosphoryl]oxy-2-methoxycarbonyl-8-azabicyclo[3.2.1]octan-8-yl]hexanoylamino]propanoic acid
  参考文献：
  名称：

  Cocaine catalytic antibodies: the primary importance of linker effects

  摘要：

  Current treatments for cocaine addiction are not effective. The development of a catalytic monoclonal antibody (mAb) provides a strategy for not only binding, but also degrading cocaine, which offers a broad-based therapy. Hapten design is the central element for programming antibody catalysis. The characteristics of the linker used in classic transition-state analogue phosphonate haptens were shown to be important for obtaining mAbs that hydrolyze the benzoate ester of cocaine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00659-4
• 作为产物：
  描述：

  苯膦酰二氯 在 三乙胺 、 lithium diisopropyl amide 、 氯甲酸-2,2,2-三氯乙酯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 methyl (1R,2R,3S,5S)-8-[6-[(2-methylpropan-2-yl)oxy]-6-oxohexyl]-3-(oxido-phenyl-phenylmethoxyphosphaniumyl)oxy-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Cocaine catalytic antibodies: the primary importance of linker effects

  摘要：

  Current treatments for cocaine addiction are not effective. The development of a catalytic monoclonal antibody (mAb) provides a strategy for not only binding, but also degrading cocaine, which offers a broad-based therapy. Hapten design is the central element for programming antibody catalysis. The characteristics of the linker used in classic transition-state analogue phosphonate haptens were shown to be important for obtaining mAbs that hydrolyze the benzoate ester of cocaine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00659-4

文献信息

• Cocaine catalytic antibodies: the primary importance of linker effects
  作者：Masayuki Matsushita、Timothy Z Hoffman、Jon A Ashley、Bin Zhou、Peter Wirsching、Kim D Janda

  DOI：10.1016/s0960-894x(00)00659-4

  日期：2001.1

  Current treatments for cocaine addiction are not effective. The development of a catalytic monoclonal antibody (mAb) provides a strategy for not only binding, but also degrading cocaine, which offers a broad-based therapy. Hapten design is the central element for programming antibody catalysis. The characteristics of the linker used in classic transition-state analogue phosphonate haptens were shown to be important for obtaining mAbs that hydrolyze the benzoate ester of cocaine. (C) 2001 Elsevier Science Ltd. All rights reserved.