(2S,3R)-O-(n-dodecanoyl)-L-threonine | 1224699-54-0

• 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: (2S,3R)-O-(n-dodecanoyl)-L-threonine
• 英文别名: (2S,3R)-2-amino-3-dodecanoyloxybutanoic acid
• CAS: 1224699-54-0
• 化学式: C₁₆H₃₁NO₄
• 分子量: 301.426
• InChiKey: AXEGKYOLSDTSKS-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 L-苏氨酸 在 三氟乙酸 、 三乙胺 作用下， 以 水 为溶剂， 反应 12.5h， 以94%的产率得到(2S,3R)-O-(n-dodecanoyl)-L-threonine
  参考文献：
  名称：

  Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone

  摘要：

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.022