(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 | 835629-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (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
• 英文别名: [(1R,2R)-2-[(1R)-2-(benzenesulfonyl)-1-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]ethyl]cyclopropyl]oxy-tert-butyl-dimethylsilane
• CAS: 835629-40-8
• 化学式: C₂₆H₄₂N₂O₅SSi
• 分子量: 522.781
• InChiKey: MBUOVUCVODFRLB-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 盐酸 、 甲醇 、 sodium amalgam 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (2S,3R,1'R,2'R)-2-amino-3-(2'-methoxymethoxy-cyclopropyl)-butyric acid methyl ester
  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：

  (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 、 (-)-(1R,2R)-2-(2-benzenesulfonylvinyl)-1-tert-butyldimethylsililoxy-cyclopropane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以95%的产率得到(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
  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