dimethyl (2S,3S)-2,3-O-(3-pentylidene)tartrate | 1233402-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl (2S,3S)-2,3-O-(3-pentylidene)tartrate
• CAS: 1233402-32-8
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: OMXPSRLKRYONFO-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl (2S,3S)-2,3-O-(3-pentylidene)tartrate 在 甲醇 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 27.34h， 生成 (2R,3R)-1,4-di-O-benzyl-2,3-O-(3-pentylidene)threitol
  参考文献：
  名称：

  An optimized synthetic route for the preparation of the versatile chiral building block 1,4-di-O-benzylthreitol

  摘要：

  An improved five-step procedure has been applied to synthesize enantiopure l- and d-1,4-di-O-benzylthreitol out of readily available l- and d-tartaric acid. Through the use of modern reagents and enhanced work-up conditions these useful auxiliaries were obtained in quite perfect yields. In addition, accurate H-1 and C-13 NMR resonance assignments of all synthesized compounds were performed by 2D NMR spectroscopy.

  DOI：

  10.1007/s00706-013-1100-x
• 作为产物：
  描述：

  D-(-)-酒石酸二甲酯 、 3-戊酮 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 反应 48.0h， 以97%的产率得到dimethyl (2S,3S)-2,3-O-(3-pentylidene)tartrate
  参考文献：
  名称：

  An optimized synthetic route for the preparation of the versatile chiral building block 1,4-di-O-benzylthreitol

  摘要：

  An improved five-step procedure has been applied to synthesize enantiopure l- and d-1,4-di-O-benzylthreitol out of readily available l- and d-tartaric acid. Through the use of modern reagents and enhanced work-up conditions these useful auxiliaries were obtained in quite perfect yields. In addition, accurate H-1 and C-13 NMR resonance assignments of all synthesized compounds were performed by 2D NMR spectroscopy.

  DOI：

  10.1007/s00706-013-1100-x