(1S,2R)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester | 129569-18-2

• 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,2R)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester
• 英文别名: ethyl (1S,2R)-2-[(1R)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]cyclopropane-1-carboxylate
• CAS: 129569-18-2
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: UTNMEKIXRXYAIQ-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R)-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,2R)-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
• 作为产物：
  描述：

  (-)-tert-butyl [(1R)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate 在 palladium diacetate camphor-10-sulfonic acid 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 16.0h， 生成 (1S,2R)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester
  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

• OFUNA, YASUSI;SIMAMOTO, KEHJKO;SINODZAKI, ATSUXIKO;ISIDA, MITIKO
  作者：OFUNA, YASUSI、SIMAMOTO, KEHJKO、SINODZAKI, ATSUXIKO、ISIDA, MITIKO

  DOI：——

  日期：——
• YAMANOI, KEIKO;OHFUNE, YASUFUMI;WATANABE, KAZUKO;NOVALES, LI PHILIPP;TAKE+, TETRAHEDRON LETT., 29,(1988) N 10, 1181-1184
  作者：YAMANOI, KEIKO、OHFUNE, YASUFUMI、WATANABE, KAZUKO、NOVALES, LI PHILIPP、TAKE+

  DOI：——

  日期：——