(2R,3R)-2,3-O-(3-pentylidene)threitol | 1472686-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2,3-O-(3-pentylidene)threitol
• CAS: 1472686-44-4
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: IVGCZRANIIXWJS-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-O-(3-pentylidene)threitol 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 26.67h， 以88%的产率得到(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：

  dimethyl (2S,3S)-2,3-O-(3-pentylidene)tartrate 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.67h， 以95%的产率得到(2R,3R)-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