(2S,4R)-2-ethyl 1-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate | 1062096-58-5

• 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,4R)-2-ethyl 1-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
• 英文别名: N-methoxycarbonyl-L-hydroxyproline ethyl ester；2-O-ethyl 1-O-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 1062096-58-5
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: BTFPQCAEAYNQGT-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,4R)-2-ethyl 1-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 以 乙腈 为溶剂， 以94%的产率得到2-O-ethyl 1-O-methyl (2S,4R)-4-hydroxy-5-methoxypyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Chiral azabicyclo-N-oxyls mediated enantioselective electrooxidation of sec-alcohols

  摘要：

  Enantiomerically pure azabicyclo-N-oxyls were prepared from L-hydroxyproline. They mediated enantioselective electrooxidation of racemic sec-alcohols to afford optically active sec-alcohols with moderate to high s value (up to 21) (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.112
• 作为产物：
  描述：

  氯甲酸甲酯 、 (4R)-4-羟基-L-脯氨酸乙酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S,4R)-2-ethyl 1-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Chiral azabicyclo-N-oxyls mediated enantioselective electrooxidation of sec-alcohols

  摘要：

  Enantiomerically pure azabicyclo-N-oxyls were prepared from L-hydroxyproline. They mediated enantioselective electrooxidation of racemic sec-alcohols to afford optically active sec-alcohols with moderate to high s value (up to 21) (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.112

文献信息

• A formal synthesis of (+)-lactacystin from 4-hydroxyproline
  作者：David K. Mycock、Paul A. Glossop、William Lewis、Christopher J. Hayes

  DOI：10.1016/j.tetlet.2012.10.076

  日期：2013.1

  A formal synthesis of (+)-lactacystin has been completed from trans-4-hydroxyproline, using a diastereoselective enolate acylation reaction as a key step. Diastereoselectivity was seen to vary as a function of the steric bulk of the C4-O-protecting group, and contrary to expectations, the best diastereoselectivities were obtained when the small methyl carbonate protecting group was used. The formal

  使用非对映选择性烯酸酯酰化反应作为关键步骤，已由反式-4-羟基脯氨酸完成了（+）-lactacystin的正式合成。观察到非对映选择性随C4-O-保护基的空间体积而变化，并且与预期相反，当使用小的碳酸甲酯保护基时，获得了最佳的非对映选择性。然后通过拦截Shibasaki的路线，通过碳酸甲酯脱保护，脱水，3-吡咯啉至3-吡咯啉酮氧化，氢化和N -CO 2 Me脱保护，来完成正式合成。