(4S,5S)-4,5-bis[(2-methylpropan-2-yl)oxymethyl]-2-(4-phenylphenyl)-1,3-dioxolane | 166248-42-6

• 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: (4S,5S)-4,5-bis[(2-methylpropan-2-yl)oxymethyl]-2-(4-phenylphenyl)-1,3-dioxolane
• CAS: 166248-42-6
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: BKUBPCKKWYALPG-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cyclopentylmagnesium chloride 、 (4S,5S)-4,5-bis[(2-methylpropan-2-yl)oxymethyl]-2-(4-phenylphenyl)-1,3-dioxolane 以 乙醚 、 苯 为溶剂， 反应 10.0h， 生成 、 (2S,3S)-3-[(S)-cyclopentyl-(4-phenylphenyl)methoxy]-1,4-bis[(2-methylpropan-2-yl)oxy]butan-2-ol
  参考文献：
  名称：

  Highly Diastereoselective Ring-Opening Reactions of Chiral Acetals with Secondary or Sterically Hindered Grignard Reagents

  摘要：

  There has been an increasing interest in the stereoselective ring opening of acetals by means of nucleophiles.(1-4) Most of these approaches involve the preferential complex formation of acetals with a Lewis acid and subsequent invertive substitution by nucleophiles (Scheme 1).(2) The retentive ring cleavage of acetals has been investigated only briefly, mostly related to the reductive ring opening with metal hydrides.(3,4) Recently, Yamamoto and his co-workers reported the highly diastereoselective retentive alkylation of chiral acetals using novel organoaluminum reagents.(4) However, only methyl- or primary alkylaluminum reagents can be used. We now wish to describe our investigations on the highly diastereoselective reactions of secondary or sterically bulky Grignard reagents with chiral acetals prepared from aldehydes and tunable chiral diols.

  DOI：

  10.1021/jo00105a041
• 作为产物：
  描述：

  1.2;3.4-Di-O-isopropyliden-D-threit 在 三甲基氯硅烷 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 44.0h， 生成 (4S,5S)-4,5-bis[(2-methylpropan-2-yl)oxymethyl]-2-(4-phenylphenyl)-1,3-dioxolane
  参考文献：
  名称：

  Highly Diastereoselective Ring-Opening Reactions of Chiral Acetals with Secondary or Sterically Hindered Grignard Reagents

  摘要：

  There has been an increasing interest in the stereoselective ring opening of acetals by means of nucleophiles.(1-4) Most of these approaches involve the preferential complex formation of acetals with a Lewis acid and subsequent invertive substitution by nucleophiles (Scheme 1).(2) The retentive ring cleavage of acetals has been investigated only briefly, mostly related to the reductive ring opening with metal hydrides.(3,4) Recently, Yamamoto and his co-workers reported the highly diastereoselective retentive alkylation of chiral acetals using novel organoaluminum reagents.(4) However, only methyl- or primary alkylaluminum reagents can be used. We now wish to describe our investigations on the highly diastereoselective reactions of secondary or sterically bulky Grignard reagents with chiral acetals prepared from aldehydes and tunable chiral diols.

  DOI：

  10.1021/jo00105a041

文献信息

• Highly Diastereoselective Ring-Opening Reactions of Chiral Acetals with Secondary or Sterically Hindered Grignard Reagents
  作者：Tien-Min Yuan、Sue-Min Yeh、Yu-Tsai Hsieh、Tien-Yau Luh

  DOI：10.1021/jo00105a041

  日期：1994.12

  There has been an increasing interest in the stereoselective ring opening of acetals by means of nucleophiles.(1-4) Most of these approaches involve the preferential complex formation of acetals with a Lewis acid and subsequent invertive substitution by nucleophiles (Scheme 1).(2) The retentive ring cleavage of acetals has been investigated only briefly, mostly related to the reductive ring opening with metal hydrides.(3,4) Recently, Yamamoto and his co-workers reported the highly diastereoselective retentive alkylation of chiral acetals using novel organoaluminum reagents.(4) However, only methyl- or primary alkylaluminum reagents can be used. We now wish to describe our investigations on the highly diastereoselective reactions of secondary or sterically bulky Grignard reagents with chiral acetals prepared from aldehydes and tunable chiral diols.