methyl (3S,4S)-4-(O-t-butyldimethylsilyl)hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylate | 171514-06-0

• 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: methyl (3S,4S)-4-(O-t-butyldimethylsilyl)hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylate
• 英文别名: methyl (5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-1,4,5,6-tetrahydropyridazine-6-carboxylate
• CAS: 171514-06-0
• 化学式: C₁₂H₂₄N₂O₃Si
• 分子量: 272.42
• InChiKey: RHAMNAXXPBQTRE-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 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：
  59.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S,4S)-4-(O-t-butyldimethylsilyl)hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylate 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 3(S)-carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine
  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 2,6-二甲基吡啶 、 二甲基硫 、 (S)-BiphempRuBr₂ 、 水 、 氢气 、 臭氧 、 三苯基膦 、 三氟乙酸 、 lithium diisopropyl amide 、 zinc methyl bromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -78.0~80.0 ℃ 、600.0 kPa 条件下， 反应 18.92h， 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

文献信息

• 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.