(3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-2-oxooctahydro-7aH-indole-7a-carboxylic acid | 1185252-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-2-oxooctahydro-7aH-indole-7a-carboxylic acid
• CAS: 1185252-54-3
• 化学式: C₁₉H₂₅NO₅S
• 分子量: 379.477
• InChiKey: ASHDQJSYWNTDDR-OALUTQOASA-N

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-2-oxooctahydro-7aH-indole-7a-carboxylic acid 在 trityl tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以85%的产率得到(3aS,7aR)-3a-hydroxy-1-(4-methoxybenzyl)-2-oxooctahydro-7aH-indole-7a-carboxylic acid
  参考文献：
  名称：

  Propellane as a conformational device for the stabilization of the β-lactone of salinosporamide A

  摘要：

  The synthesis of a propellane derivative of salinosporamide A having increased stability under physiological-like conditions is reported. The synthesis took advantage of a substrate-controlled stereoselective Ugi 4-center 3-component reaction to construct the required syn-bicyclic pyroglutamic acid framework. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.085
• 作为产物：
  描述：

  (3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-7a-(1H-indol-1-ylcarbonyl)octahydro-2H-indol-2-one 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以77%的产率得到(3aS,7aR)-1-(4-methoxybenzyl)-3a-[(methylsulfanyl)-methoxy]-2-oxooctahydro-7aH-indole-7a-carboxylic acid
  参考文献：
  名称：

  Propellane as a conformational device for the stabilization of the β-lactone of salinosporamide A

  摘要：

  The synthesis of a propellane derivative of salinosporamide A having increased stability under physiological-like conditions is reported. The synthesis took advantage of a substrate-controlled stereoselective Ugi 4-center 3-component reaction to construct the required syn-bicyclic pyroglutamic acid framework. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.085