methyl-(2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-hydroxyoct-5(E)-enoate | 171514-04-8

• 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: methyl-(2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-hydroxyoct-5(E)-enoate
• 英文别名: methyl (E,2S,3S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]oct-5-enoate
• CAS: 171514-04-8
• 化学式: C₁₉H₃₄N₂O₇
• 分子量: 402.488
• InChiKey: BHXSSXAZEXFGNP-NKVPIJFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl-(2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-hydroxyoct-5(E)-enoate 在 2,6-二甲基吡啶 、 二甲基硫 、 水 、 臭氧 、 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.42h， 生成 methyl (3S,4S)-4-(O-t-butyldimethylsilyl)hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylate
  参考文献：
  名称：

  Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A.

  摘要：

  The enantioselective synthesis of (3S, 4S)4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid 1 is described. The two stereogenic centers in anti relationship are obtained by sequential enantio and chemoselective hydrogenation of beta-ketoester in presence of chiral ruthenium catalyst and diastereoselective amination of beta-hydroxyester with di t-butylazodicarboxylate.

  DOI：

  10.1016/0957-4166(95)00258-q
• 作为产物：
  描述：

  Methyl (E)-3-oxooct-5-enoate 在 (S)-BiphempRuBr₂ 、 氢气 、 lithium diisopropyl amide 、 zinc methyl bromide 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、600.0 kPa 条件下， 反应 0.5h， 生成 methyl-(2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-hydroxyoct-5(E)-enoate
  参考文献：
  名称：

  Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A.

  摘要：

  The enantioselective synthesis of (3S, 4S)4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid 1 is described. The two stereogenic centers in anti relationship are obtained by sequential enantio and chemoselective hydrogenation of beta-ketoester in presence of chiral ruthenium catalyst and diastereoselective amination of beta-hydroxyester with di t-butylazodicarboxylate.

  DOI：

  10.1016/0957-4166(95)00258-q

文献信息

• Enantioselective ruthenium-mediated hydrogenation: developments and applications
  作者：Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/s0022-328x(98)00680-9

  日期：1998.9

  A general preparation of chiral ruthenium(II) catalysts and the homogeneous enantioselective hydrogenation of prochiral olefins and keto groups are presented. Some applications to the synthesis of biologically active compounds are reported. (C) 1998 Elsevier Science S.A. All rights reserved.
• Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A.
  作者：Christine Greck、Laurent Bischoff、Jean Pierre Genêt

  DOI：10.1016/0957-4166(95)00258-q

  日期：1995.8

  The enantioselective synthesis of (3S, 4S)4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid 1 is described. The two stereogenic centers in anti relationship are obtained by sequential enantio and chemoselective hydrogenation of beta-ketoester in presence of chiral ruthenium catalyst and diastereoselective amination of beta-hydroxyester with di t-butylazodicarboxylate.