bis(1-methylethyl) (4R)-trans-2-methyl-2-methoxy-1,3-dioxolan-4,5-dicarboxylate | 140430-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(1-methylethyl) (4R)-trans-2-methyl-2-methoxy-1,3-dioxolan-4,5-dicarboxylate
• 英文别名: dipropan-2-yl (4R,5R)-2-methoxy-2-methyl-1,3-dioxolane-4,5-dicarboxylate
• CAS: 140430-21-3
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: VQCKTJLYVHDDII-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-环己烯氧基三甲基硅烷 、 bis(1-methylethyl) (4R)-trans-2-methyl-2-methoxy-1,3-dioxolan-4,5-dicarboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到bis(1-methylethyl) (4R)-trans-2-methyl-2-(2-oxocyclohexyl)-1,3-dioxolan-4,5-dicarboxylate
  参考文献：
  名称：

  Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers

  摘要：

  Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.

  DOI：

  10.1016/s0040-4020(01)90792-6
• 作为产物：
  描述：

  原乙酸三甲酯 、 L-(+)-酒石酸二异丙酯 在 硫酸 作用下， 以 苯 为溶剂， 以60%的产率得到bis(1-methylethyl) (4R)-trans-2-methyl-2-methoxy-1,3-dioxolan-4,5-dicarboxylate
  参考文献：
  名称：

  Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers

  摘要：

  Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.

  DOI：

  10.1016/s0040-4020(01)90792-6

文献信息

• Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers
  作者：Luigi Longobardo、Giovanna Mobbili、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1016/s0040-4020(01)90792-6

  日期：1992.1

  Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.