ethyl (1S,2S,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-dihydroxycyclopentanecarboxylate | 1006611-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1S,2S,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-dihydroxycyclopentanecarboxylate
• 英文别名: ethyl (1S,2S,3R,4S)-3,4-dihydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate
• CAS: 1006611-44-4
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: UXNCSGJYZMICRH-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2S,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-dihydroxycyclopentanecarboxylate 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  A new strategy for the preparation of heterocyclic β-amino esters: orthogonally protected β-amino esters with a piperidine skeleton

  摘要：

  A simple strategy is presented for the introduction of a nitrogen atom into the carbocycle of an aminocyclopentene-carboxylic ester via dihydroxylation of the olefinic bond, followed by NaIO4-mediated cleavage of the diol intermediate and ring expansion, resulting in new regioisomeric 3-amino-4-piperidinecarboxylic acid derivatives. This method permits the preparation of amino esters with a piperidine skeleton in enantiomerically pure form. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.043
• 作为产物：
  描述：

  ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate 在 potassium permanganate 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以46%的产率得到ethyl (1S,2S,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-dihydroxycyclopentanecarboxylate
  参考文献：
  名称：

  A new strategy for the preparation of heterocyclic β-amino esters: orthogonally protected β-amino esters with a piperidine skeleton

  摘要：

  A simple strategy is presented for the introduction of a nitrogen atom into the carbocycle of an aminocyclopentene-carboxylic ester via dihydroxylation of the olefinic bond, followed by NaIO4-mediated cleavage of the diol intermediate and ring expansion, resulting in new regioisomeric 3-amino-4-piperidinecarboxylic acid derivatives. This method permits the preparation of amino esters with a piperidine skeleton in enantiomerically pure form. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.043