2-oxo-3-(triisopropylsilyloxy)propionic acid ethyl ester | 464911-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxo-3-(triisopropylsilyloxy)propionic acid ethyl ester
• 英文别名: Ethyl 2-oxo-3-tri(propan-2-yl)silyloxypropanoate
• CAS: 464911-14-6
• 化学式: C₁₄H₂₈O₄Si
• 分子量: 288.459
• InChiKey: JNGCSCAXHDIYTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-3-(triisopropylsilyloxy)propionic acid ethyl ester 在 锂硼氢 、 四氯化锡 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 Methanesulfonic acid (2S,3S,4R,5S)-4-(dimethyl-phenyl-silanyl)-3-hydroxy-4,5-dimethyl-2-triisopropylsilanyloxymethyl-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of (±)-5-epi-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation

  摘要：

  The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.

  DOI：

  10.1021/ol026343e
• 作为产物：
  描述：

  ethyl 2,3-dihydroxypropionate 在 咪唑 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-oxo-3-(triisopropylsilyloxy)propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of (±)-5-epi-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation

  摘要：

  The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.

  DOI：

  10.1021/ol026343e

文献信息

• Synthesis of (±)-5-<i>e</i><i>pi</i>-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation
  作者：Zhi-Hui Peng、K. A. Woerpel

  DOI：10.1021/ol026343e

  日期：2002.8.1

  The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.