(1S,2S)-2-((R)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid | 129569-91-1

• 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: (1S,2S)-2-((R)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid
• CAS: 129569-91-1
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: XEXZEHHDYJHEND-LYFYHCNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-((R)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4R) α-(Carboxycyclopropyl)glycine
  参考文献：
  名称：

  Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

  摘要：

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.

  DOI：

  10.1021/jo00013a018
• 作为产物：
  描述：

  (1S,2S)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester 在 sodium hydroxide 、 jones reagent 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 生成 (1S,2S)-2-((R)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

  摘要：

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.

  DOI：

  10.1021/jo00013a018

文献信息

• A concise and efficient stereoselective synthesis of protected (2R,1′S,2′S)-2-(carboxycyclopropyl)glycine (D-CCG-I)
  作者：Debendra K. Mohapatra

  DOI：10.1039/b105503h

  日期：——

  The stereoselective synthesis of protected D-carboxycyclopropylglycine (D-CCG-I) was achieved, as an extension of Taguchi's protocol for Simmons–Smith cyclopropanation to a chiral, amino-containing allyl alcohol derivative, in 8 steps (40% overall yield).

  受保护的D-羧基环丙基甘氨酸（D-CCG-I）的立体选择性合成得以实现，作为田口协议对西蒙斯-史密斯环丙烷化反应的扩展，以8个步骤（总产率为40%）将手性、含氨基的烯丙醇衍生物转化为手性、含氨基的烯丙醇衍生物。