(2SR,3RS)-1-acetamido-4-diphenylphosphinoyl-3-methylbutane-2,3-diol

• 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: (2SR,3RS)-1-acetamido-4-diphenylphosphinoyl-3-methylbutane-2,3-diol
• 英文别名: N-[(2S,3R)-4-diphenylphosphoryl-2,3-dihydroxy-3-methylbutyl]acetamide
• 化学式: C₁₉H₂₄NO₄P
• 分子量: 361.378
• InChiKey: KLZAFFZREIJMIV-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R)-1-diphenylphosphoryl-2-[(2S)-oxiran-2-yl]propan-2-ol 在 palladium on activated charcoal sodium azide 、 氢气 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇甲醚 、 水 为溶剂， 反应 24.75h， 生成 (2SR,3RS)-1-acetamido-4-diphenylphosphinoyl-3-methylbutane-2,3-diol
  参考文献：
  名称：

  Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcohols

  摘要：

  Regioselective ring-openings of epoxy alcohols bearing a diphenylphosphinoyl (Ph(2)PO) group give diols which can undergo stereospecific Horner-Wittig elimination. This method was used to make allylic alcohols, unsaturated beta-hydroxy sulfides, homoallylic alcohols and unsaturated amino acids, with control over their absolute (R,S), relative (syn,anti) and geometrical(E,Z) stereochemistry.

  DOI：

  10.1039/p19950001913

文献信息

• Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcohols
  作者：Jonathan Clayden、Andrew B. McElroy、Stuart Warren

  DOI：10.1039/p19950001913

  日期：——

  Regioselective ring-openings of epoxy alcohols bearing a diphenylphosphinoyl (Ph(2)PO) group give diols which can undergo stereospecific Horner-Wittig elimination. This method was used to make allylic alcohols, unsaturated beta-hydroxy sulfides, homoallylic alcohols and unsaturated amino acids, with control over their absolute (R,S), relative (syn,anti) and geometrical(E,Z) stereochemistry.