(2R,3R)-tert-butyl 4-amino-2,3-dihydroxy-2-methylbutanoate | 1025915-53-0

• 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: (2R,3R)-tert-butyl 4-amino-2,3-dihydroxy-2-methylbutanoate
• 英文别名: tert-butyl (2R,3R)-4-amino-2,3-dihydroxy-2-methylbutanoate
• CAS: 1025915-53-0
• 化学式: C₉H₁₉NO₄
• 分子量: 205.254
• InChiKey: QYSSJIGMMHZHJP-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-tert-butyl 4-amino-2,3-dihydroxy-2-methylbutanoate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoic acid
  参考文献：
  名称：

  First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

  摘要：

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.051
• 作为产物：
  描述：

  2,3-O-isopropylidene-2-C-methyl-D-erythritol 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 偶氮二甲酸二异丙酯 、 palladium on activated charcoal 、 四丁基氟化铵 、 水 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 碳酸氢钠 、 sodium carbonate 、 乙二胺 、 三苯基膦 、 potassium bromide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 109.58h， 生成 (2R,3R)-tert-butyl 4-amino-2,3-dihydroxy-2-methylbutanoate
  参考文献：
  名称：

  Total Synthesis of Enantiopure Potassium Aeshynomate

  摘要：

  Potassium aeshynomate (1) is the leaf-opening factor of the nyctinastic plant Aeshynomene indica L. In this article a convenient and efficient strategy for the total synthesis of enantiomerically pure 1 is described, starting from the L-arabinose derived chiron ent-6. The realized synthetic scheme involves a postcoupling oxidation approach and securely determines the absolute configuration of the targeted natural product, which remained unknown until now.

  DOI：

  10.1021/jo5011735

文献信息

• First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers
  作者：Stéphanie Claudel、Tomasz Krzysztof Olszewski、Pierre Mutzenardt、Christie Aroulanda、Philippe Coutrot、Claude Grison

  DOI：10.1016/j.tet.2005.11.051

  日期：2006.2

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Enantiopure Potassium Aeshynomate
  作者：Stergios R. Rizos、John G. Stefanakis、Stefanos S. Kotoulas、Alexandros E. Koumbis

  DOI：10.1021/jo5011735

  日期：2014.7.18

  Potassium aeshynomate (1) is the leaf-opening factor of the nyctinastic plant Aeshynomene indica L. In this article a convenient and efficient strategy for the total synthesis of enantiomerically pure 1 is described, starting from the L-arabinose derived chiron ent-6. The realized synthetic scheme involves a postcoupling oxidation approach and securely determines the absolute configuration of the targeted natural product, which remained unknown until now.