(2S,5R,2'R,1''R,2''R)-2'-[2-amino-4-benzenesulfonyl-3-(2''-hydroxy-cyclopropyl)-butyrylamino]-3'-methyl-butyric acid methyl ester | 835629-42-0

• 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: (2S,5R,2'R,1''R,2''R)-2'-[2-amino-4-benzenesulfonyl-3-(2''-hydroxy-cyclopropyl)-butyrylamino]-3'-methyl-butyric acid methyl ester
• 英文别名: methyl (2R)-2-[[(2S,3R)-2-amino-4-(benzenesulfonyl)-3-[(1R,2R)-2-hydroxycyclopropyl]butanoyl]amino]-3-methylbutanoate
• CAS: 835629-42-0
• 化学式: C₁₉H₂₈N₂O₆S
• 分子量: 412.507
• InChiKey: YMZPDTWSPGASRZ-OVYGPGRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  135.79
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,5R,2'R,1''R,2''R)-2'-[2-amino-4-benzenesulfonyl-3-(2''-hydroxy-cyclopropyl)-butyrylamino]-3'-methyl-butyric acid methyl ester 、 乙酸酐 在 吡啶 作用下， 反应 21.0h， 以78%的产率得到(2S,3R,2'R,1''R,2''R)-2'-[3-(2''-acetoxy-cyclopropyl)-2-acetylamino-4-benzenesulfonyl-butyrylamino]-3'-methyl-butyric acid methyk 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：

  (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 四丁基氟化铵 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以84%的产率得到(2S,5R,2'R,1''R,2''R)-2'-[2-amino-4-benzenesulfonyl-3-(2''-hydroxy-cyclopropyl)-butyrylamino]-3'-methyl-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