(1R,2S,5S)-4-Oxo-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester | 167423-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,5S)-4-Oxo-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester
• 英文别名: (1R,2S,5S)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-oxo-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• CAS: 167423-77-0
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: KWBCGWBKQFQJAO-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,5S)-4-Oxo-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以72%的产率得到N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropane α-amino acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-methanoproline and N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid

  摘要：

  The tide compounds were synthesized by a S-step facile transformation of the key intermediate 4, itself obtained by a ''one-pot'' sulfone-mediated cyclopropanation from chiral synthon (R)-I and (2R)-glycidyl triflate.

  DOI：

  10.1016/0040-4039(95)00482-r
• 作为产物：
  描述：

  [(R)-1-(1-Benzenesulfonyl-2-hydroxymethyl-cyclopropyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 生成 (1S,2S)-2-[(S)-carboxy-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclopropane-1-carboxylic acid 、 (1R,2S,5S)-4-Oxo-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of cyclopropane α-amino acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-methanoproline and N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid

  摘要：

  The tide compounds were synthesized by a S-step facile transformation of the key intermediate 4, itself obtained by a ''one-pot'' sulfone-mediated cyclopropanation from chiral synthon (R)-I and (2R)-glycidyl triflate.

  DOI：

  10.1016/0040-4039(95)00482-r

文献信息

• Enantioselective synthesis of cyclopropane α-amino acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-methanoproline and N-Boc-(2S,3R,4S)-3,4-methanoglutamic acid
  作者：Isabelle Sagnard、N.André Sasaki、Angèle Chiaroni、Claude Riche、Pierre Potier

  DOI：10.1016/0040-4039(95)00482-r

  日期：1995.5

  The tide compounds were synthesized by a S-step facile transformation of the key intermediate 4, itself obtained by a ''one-pot'' sulfone-mediated cyclopropanation from chiral synthon (R)-I and (2R)-glycidyl triflate.