Methanesulfonic acid (2S,3R)-3-(diphenyl-phosphinoylmethyl)-3-methyl-oxiranylmethyl ester

• 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: Methanesulfonic acid (2S,3R)-3-(diphenyl-phosphinoylmethyl)-3-methyl-oxiranylmethyl ester
• 英文别名: [(2S,3R)-3-(diphenylphosphorylmethyl)-3-methyloxiran-2-yl]methyl methanesulfonate
• 化学式: C₁₈H₂₁O₅PS
• 分子量: 380.402
• InChiKey: MTAXQXVZSXGHDU-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基磺酰氯 、 (2R,3S)-4-diphenylphosphinoyl-2,3-epoxy-3-methylbutan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 Methanesulfonic acid (2S,3R)-3-(diphenyl-phosphinoylmethyl)-3-methyl-oxiranylmethyl ester 、 (2S,3S)-4-diphenylphosphinoyl-2,3-epoxy-3-methylbutyl methanesulfonate
  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.