ethyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>prolinate | 180844-08-0

• 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: ethyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>prolinate
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2S,3S,4R)-3,4-dideuteriopyrrolidine-1,2-dicarboxylate
• CAS: 180844-08-0
• 化学式: C₁₂H₂₁NO₄
• 分子量: 245.287
• InChiKey: IBCLKOLOJLBQDZ-OBNCYELVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>prolinate 在 盐酸 、 ruthenium(IV) oxide 、 sodium periodate 、 三氟化硼乙醚 、 triethylgermane-d₁ 、 三乙基硼氢化锂 作用下， 生成 (2S,3S,4R,5S)-<3,4,5-D3>proline
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S,4R,5S)-proline-3,4,5-d3

  摘要：

  A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCl2(PPh3)(3) followed by RuO4-oxidatian gave a 3,4-dideuterated L-pyroglutamic acid derivative which is considered to be a promising precursor far various deuterated amino acids. The present study demonstrates a stereoselective reduction of the amide carbonyl moiety leading to L-proline derivatives in which all of the ring methylenes are stereoselectively labeled with deuterium. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01189-1
• 作为产物：
  描述：

  ethyl (2S)-N-t-butoxycarbonyl-3,4-dehydroprolinate 在 tris(triphenylphosphine)ruthenium(II) chloride 、 氘 作用下， 以 氘代甲醇-d 、 苯 为溶剂， 以100%的产率得到ethyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>prolinate
  参考文献：
  名称：

  Asymmetric synthesis of l-proline regio- and stereoselectively labelled with deuterium

  摘要：

  A synthesis of L-proline where all of the ring methylenes me stereoselectiveiy labelled with deuterium is described. A catalytic deuteration of protected 3,4-dehydro-L-proline using transition metal catalyst followed by RuO4-oxidation gave a [3,4-D-2]pyroglutamic acid derivative. A syn-selective deuteration of the aminal derived from the pyroglutamate with Et3SiD-BF3. OEt2 furnished (2S,3S,4R,5S)-[3,4,5-D-3]proline. The present procedure is also applied to the synthesis of the corresponding (2S,3S,4R,SR)-isomer. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00083-x

文献信息

• Evidence for a Stereoelectronic Effect in Human Oxygen Sensing
  作者：Christoph Loenarz、Jasmin Mecinović、Rasheduzzaman Chowdhury、Luke A. McNeill、Emily Flashman、Christopher J. Schofield

  DOI：10.1002/anie.200805427

  日期：2009.2.23

  trans‐4‐prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate‐analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen‐sensing hydroxylases (PHDs) achieve specificity for hydroxyprolyl/prolyl residues for the C4‐exo/endo prolyl conformations, respectively.

  PHD如何达到特异性：转录因子HIF的反式-4-脯氨酰羟化反应具有立体化学保留。基板类似物的研究表明该林-希肿瘤抑制蛋白（VHL蛋白）和氧传感羟化酶（博士）如何实现羟基脯/脯氨酰残基为C特异性4 -外型/内型分别脯氨酰构象。