Ethyl (4S,2E)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butoxycarbonyl)amino]pent-2-enoate | 125982-21-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (4S,2E)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butoxycarbonyl)amino]pent-2-enoate
• 英文别名: ethyl (E,4S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pent-2-enoate
• CAS: 125982-21-0
• 化学式: C₁₈H₃₅NO₅Si
• 分子量: 373.565
• InChiKey: NBKAGMRCLKTYTB-GETOMWPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl (4S,2E)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butoxycarbonyl)amino]pent-2-enoate 、 溴丁基-镁 、 碘化亚铜 生成 ethyl (3R)-3-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]heptanoate
  参考文献：
  名称：

  YODA, HIDEMI;NAITO, SATOSHI;TAKABE, KUNIHIKO;TANAKA, NOBUO;HOSOYA, KEN, CHEM. EXPRESS., 4,(1989) N, C. 585-588

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (4S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylpentanoate 生成 Ethyl (4S,2E)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butoxycarbonyl)amino]pent-2-enoate
  参考文献：
  名称：

  YODA, HIDEMI;NAITO, SATOSHI;TAKABE, KUNIHIKO;TANAKA, NOBUO;HOSOYA, KEN, CHEM. EXPRESS., 4,(1989) N, C. 585-588

  摘要：

  DOI：

文献信息

• Ishii, Kiyonori; Ohno, Hiroaki; Takemoto, Yoshiji, Journal of the Chemical Society. Perkin transactions I, 1999, # 15, p. 2155 - 2163
  作者：Ishii, Kiyonori、Ohno, Hiroaki、Takemoto, Yoshiji、Osawa, Eriko、Yamaoka, Yumiko、Fujii, Nobutaka、Ibuka, Toshiro

  DOI：——

  日期：——
• Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs
  作者：Keiko Shimamoto、Michiko Ishida、Haruhikio Shinozaki、Yasufumi Ohfune

  DOI：10.1021/jo00013a018

  日期：1991.6

  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.
• YODA, HIDEMI;NAITO, SATOSHI;TAKABE, KUNIHIKO;TANAKA, NOBUO;HOSOYA, KEN, CHEM. EXPRESS., 4,(1989) N, C. 585-588
  作者：YODA, HIDEMI、NAITO, SATOSHI、TAKABE, KUNIHIKO、TANAKA, NOBUO、HOSOYA, KEN

  DOI：——

  日期：——