(2S,3S)-2,3-dibenzyloxybutane | 127102-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-2,3-dibenzyloxybutane
• 英文别名: [(2R,3R)-3-phenylmethoxybutan-2-yl]oxymethylbenzene
• CAS: 127102-65-2
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: JNRXLSQFWWYZNP-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-dibenzyloxybutane 在 铂 氢气 作用下， 以48%的产率得到(2R,3R)-3-(phenylmethoxy)-2-butanol
  参考文献：
  名称：

  Enantiomeric recognition of organic ammonium salts by chiral dialkyl-, dialkenyl-, and tetramethyl-substituted pyridino-18-crown-6 and tetramethyl-substituted bispyridino-18-crown-6 ligands: comparison of temperature-dependent proton NMR and empirical force field techniques

  摘要：

  DOI：

  10.1021/jo00297a031
• 作为产物：
  描述：

  (2R,3R)-(-)-2,3-丁二醇 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(2S,3S)-2,3-dibenzyloxybutane
  参考文献：
  名称：

  Design, Synthesis, and Application of a C₂ Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated Aldimine

  摘要：

  A C-2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2-diphenylethane was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic alpha,beta-unsaturated aldimines. The absolute configuration of the product is predictable by the model.

  DOI：

  10.1021/jo9813181

文献信息

• Enantiomeric recognition of organic ammonium salts by chiral dialkyl-, dialkenyl-, and tetramethyl-substituted pyridino-18-crown-6 and tetramethyl-substituted bispyridino-18-crown-6 ligands: comparison of temperature-dependent proton NMR and empirical force field techniques
  作者：Jerald S. Bradshaw、Peter Huszthy、Christopher W. McDaniel、Cheng Y. Zhu、N. Kent Dalley、Reed M. Izatt、Shneior Lifson

  DOI：10.1021/jo00297a031

  日期：1990.5
• Design, Synthesis, and Application of a <i>C</i>₂ Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated Aldimine
  作者：Mitsuru Shindo、Kenji Koga、Kiyoshi Tomioka

  DOI：10.1021/jo9813181

  日期：1998.12.1

  A C-2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2-diphenylethane was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic alpha,beta-unsaturated aldimines. The absolute configuration of the product is predictable by the model.