(2S,5R,1'R,1''R,2''R)-2-{1'-[2''-(tert-butyl-dimethyl-silanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine | 835629-45-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,5R,1'R,1''R,2''R)-2-{1'-[2''-(tert-butyl-dimethyl-silanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
• 英文别名: tert-butyl-[(1R,2R)-2-[(1R)-1-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]ethyl]cyclopropyl]oxy-dimethylsilane
• CAS: 835629-45-3
• 化学式: C₂₀H₃₈N₂O₃Si
• 分子量: 382.619
• InChiKey: LYJGKURQEOPSLD-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R,1'R,1''R,2''R)-2-{1'-[2''-(tert-butyl-dimethyl-silanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以39%的产率得到(2S,5R,1'R,1''R,2''R)-2-[1'-(2''-hydroxy-cyclopropyl)-ethyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
  参考文献：
  名称：

  Chemistry of vinyl sulfones. Approach to novel conformationally restricted analogues of glutamic acid

  摘要：

  A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.072
• 作为产物：
  描述：

  (2S,5R,1'R,1''R,2''R)-2-{2'-benzenesulfonyl-1'-[2''-(tert-butyldimethylsilanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 在 甲醇 、 sodium amalgam 作用下， 反应 1.5h， 以82%的产率得到(2S,5R,1'R,1''R,2''R)-2-{1'-[2''-(tert-butyl-dimethyl-silanyloxy)-cyclopropyl]-ethyl}-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
  参考文献：
  名称：

  Chemistry of vinyl sulfones. Approach to novel conformationally restricted analogues of glutamic acid

  摘要：

  A totally different approach to conformationally restricted glutamic acid analogues is described, in which one of the acid functions is replaced by a cyclopropanol. The reactivity of cyclopropanol vinyl sulfones toward addition of lithiated Schollkopf bislactim ether provides a facile synthesis of a-amino acid diastereoisomers. Conformational analysis of these analogues, incorporating solvation effects, and docking to a glutamate receptor model, are used to show the relevance of the conformational restrictions employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.072