di-tert-butyl (1S,2S,4R,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate | 1359762-15-4

• 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: di-tert-butyl (1S,2S,4R,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate
• 英文别名: ditert-butyl (1S,2S,4R,5R,6S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]bicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS: 1359762-15-4
• 化学式: C₂₂H₃₇NO₆
• 分子量: 411.539
• InChiKey: FBGCZFZMYZYJLX-JAFJMASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (1S,2S,4R,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate 在 溶剂黄146 作用下， 以 水 为溶剂， 以94%的产率得到1S,2S,4R,5R,6S-2-amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylate
  参考文献：
  名称：

  Improved Synthesis of C4α- and C4β-Methyl Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylate

  摘要：

  An efficient and divergent synthesis of C4 alpha- and C4 beta-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4 alpha- or C4 beta-methyl substituent was introduced In a highly stereoselective and high-yielding manner.

  DOI：

  10.1021/ol300516y
• 作为产物：
  描述：

  tert-butyl 2-(tetrahydro-1λ⁴-thiophen-1-ylidene)acetate 在 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium tri(sec-butyl)borohydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 9.17h， 生成 di-tert-butyl (1S,2S,4R,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate
  参考文献：
  名称：

  Improved Synthesis of C4α- and C4β-Methyl Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylate

  摘要：

  An efficient and divergent synthesis of C4 alpha- and C4 beta-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4 alpha- or C4 beta-methyl substituent was introduced In a highly stereoselective and high-yielding manner.

  DOI：

  10.1021/ol300516y

文献信息

• Simple conversion of fully protected amino acids to zwitterions
  作者：Junliang Hao、Matt Reinhard、Steven S. Henry、Eric P. Seest、Matthew D. Belvo、James A. Monn

  DOI：10.1016/j.tetlet.2012.01.033

  日期：2012.3

  An operationally simple and efficient method under mild acidic conditions was developed to convert fully protected amino acids to the corresponding zwitterions without either isoelectric precipitation or ion exchange chromatography. (C) 2012 Elsevier Ltd. All rights reserved.
• Improved Synthesis of C4α- and C4β-Methyl Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylate
  作者：Steven S. Henry、Molly D. Brady、Dana L. T. Laird、J. Craig Ruble、David L. Varie、James A. Monn

  DOI：10.1021/ol300516y

  日期：2012.6.1

  An efficient and divergent synthesis of C4 alpha- and C4 beta-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4 alpha- or C4 beta-methyl substituent was introduced In a highly stereoselective and high-yielding manner.