1-tert-butyl 2-ethyl (2R,3S)-3-(benzyloxy)pyrrolidine-1,2-dicarboxylate | 1408186-89-9

• 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: 1-tert-butyl 2-ethyl (2R,3S)-3-(benzyloxy)pyrrolidine-1,2-dicarboxylate
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2R,3S)-3-phenylmethoxypyrrolidine-1,2-dicarboxylate
• CAS: 1408186-89-9
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: OCVMRIWRJKZQKX-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-ethyl (2R,3S)-3-(benzyloxy)pyrrolidine-1,2-dicarboxylate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 ethyl (2R,3S)-3-(benzyloxy)-1-((3,4-dichlorophenyl)sulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  d-Proline-based peptidomimetic inhibitors of anthrax lethal factor

  摘要：

  In this work we reported the generation of D-proline-derived hydroxamic acids as inhibitors of anthrax lethal factor (LF), taking advantage of a pyrrolidine ring as the central scaffold and a hydroxamate group as the Zn2+ chelating agent. The introduction of two hydrophobic groups addressing the S1' subsite and a long substrate-binding groove was conceived by overlapping the bioactive conformations of two reported LF inhibitors. Micromolar affinity of compound 38 suggested cis-3-substituted-1-sulfonamido-D-proline hydroxamic acids as a promising class of peptidomimetic inhibitors for developing novel LF inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.028
• 作为产物：
  描述：

  2-氮杂丁烷-1,4-二羧酸二乙酯 在 potassium tert-butylate 、 四丁基碘化铵 、 sodium hydride 、 calcium chloride 、 sodium hydroxide 、 蔗糖 作用下， 以 四氢呋喃 、 氯仿 、 水 、 甲苯 为溶剂， 反应 138.5h， 生成 1-tert-butyl 2-ethyl (2R,3S)-3-(benzyloxy)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  d-Proline-based peptidomimetic inhibitors of anthrax lethal factor

  摘要：

  In this work we reported the generation of D-proline-derived hydroxamic acids as inhibitors of anthrax lethal factor (LF), taking advantage of a pyrrolidine ring as the central scaffold and a hydroxamate group as the Zn2+ chelating agent. The introduction of two hydrophobic groups addressing the S1' subsite and a long substrate-binding groove was conceived by overlapping the bioactive conformations of two reported LF inhibitors. Micromolar affinity of compound 38 suggested cis-3-substituted-1-sulfonamido-D-proline hydroxamic acids as a promising class of peptidomimetic inhibitors for developing novel LF inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.028