(2S,3R,1'R,2'R)-3-(2'-acetoxy-cyclopropyl)-2-amino-butyric acid methyl ester | 835629-50-0

• 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,3R,1'R,2'R)-3-(2'-acetoxy-cyclopropyl)-2-amino-butyric acid methyl ester
• 英文别名: methyl (2S,3R)-3-[(1R,2R)-2-acetyloxycyclopropyl]-2-aminobutanoate
• CAS: 835629-50-0
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: YDMWSFSOLQDELX-YYNOVJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,1'R,2'R)-3-(2'-acetoxy-cyclopropyl)-2-amino-butyric acid methyl ester 以 氘代氯仿 为溶剂， 生成 (2S,3R,1'R,2'R)-2-acetylamino-3-(2'-hydroxy-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：

  (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 吡啶 、 盐酸 、 甲醇 、 sodium amalgam 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (2S,3R,1'R,2'R)-3-(2'-acetoxy-cyclopropyl)-2-amino-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

文献信息

• Chemistry of vinyl sulfones. Approach to novel conformationally restricted analogues of glutamic acid
  作者：David Díez、P. García、Isidro S. Marcos、N.M. Garrido、P. Basabe、Howard B. Broughton、Julio G. Urones

  DOI：10.1016/j.tet.2004.10.072

  日期：2005.1

  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.