4-(1'-((benzyloxy)carbonyl)-2'-(methoxycarbonyl)pyrrolidin-2'-yl)-2-aminobutanoic acid | 1421067-19-7

• 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: 4-(1'-((benzyloxy)carbonyl)-2'-(methoxycarbonyl)pyrrolidin-2'-yl)-2-aminobutanoic acid
• 英文别名: 2-Amino-4-(2-methoxycarbonyl-1-phenylmethoxycarbonylpyrrolidin-2-yl)butanoic acid；2-amino-4-(2-methoxycarbonyl-1-phenylmethoxycarbonylpyrrolidin-2-yl)butanoic acid
• CAS: 1421067-19-7
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: RUBHKYGNBHWBNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基吡咯烷-1,2-二羧酸-1-苄酯 在 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 草酰氯 、 双氧水 、 碳酸氢铵 、 2-甲基-丁烯 、 二甲基亚砜 、 三乙胺 、 potassium hydroxide 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 135.0h， 生成 4-(1'-((benzyloxy)carbonyl)-2'-(methoxycarbonyl)pyrrolidin-2'-yl)-2-aminobutanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors

  摘要：

  An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)(2)borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 mu M. (c) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.12.004

文献信息

• Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors
  作者：Wendy A. Loughlin、Stephanie S. Schweiker、Ian D. Jenkins、Luke C. Henderson

  DOI：10.1016/j.tet.2012.12.004

  日期：2013.2

  An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)(2)borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 mu M. (c) 2012 Published by Elsevier Ltd.